start-ver=1.4 cd-journal=joma no-vol=95 cd-vols= no-issue=1 article-no= start-page=390 end-page=409 dt-received= dt-revised= dt-accepted= dt-pub-year=2016 dt-pub=20161219 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Efficient Total Syntheses of Natural Neopterin Glycosides: Neopterin Glucronide and Solfapterin en-subtitle= kn-subtitle= en-abstract= kn-abstract= 1f,2f-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitro- phenyl)ethyl]neopterin (11a) and its 1f,2f-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoyl--D-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3f-O-(-D-gluco- pyranosyl)neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy--D-glucopyranosyl bromide (21b) provided the corresponding 3f-O-(-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=IwasakiKatsuya en-aut-sei=Iwasaki en-aut-mei=Katsuya kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=SaekiKaori en-aut-sei=Saeki en-aut-mei=Kaori kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=HattoriTakafumi en-aut-sei=Hattori en-aut-mei=Takafumi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= affil-num=2 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= affil-num=3 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= affil-num=4 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= END start-ver=1.4 cd-journal=joma no-vol=88 cd-vols= no-issue=2 article-no= start-page=1491 end-page=1499 dt-received= dt-revised= dt-accepted= dt-pub-year=2014 dt-pub=201404 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses en-subtitle= kn-subtitle= en-abstract= kn-abstract=The Gabriel-Isay condensation of three types of pentos-2-uloses with 2,5,6-triaminopyrimidin-4(3H)-one (3) was examined under both acidic and basic conditions. The condensation of 5-deoxy- and 5-O-protected pentofuranos-2-uloses with 3 at pH 8 afforded 6-substituted pterins as major isomers, whereas the same reaction at pH 3 yielded the 7-substituted pterins predominantly. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name=ԒJ kn-aut-sei=ԒJ kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=ItoKasumi en-aut-sei=Ito en-aut-mei=Kasumi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= affil-num=1 en-affil= kn-affil=JZ^[ affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University END start-ver=1.4 cd-journal=joma no-vol=24 cd-vols= no-issue=1 article-no= start-page=3 end-page=6 dt-received= dt-revised= dt-accepted= dt-pub-year=2013 dt-pub=201306 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of Asperopterin A, an Isoxanthopterin Glycoside from Aspergillus Oryzae en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key precursor, N-2-(N,N -dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding beta-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b). en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil=Shujitsu Univ, Sch Pharm en-keyword=asperopterin kn-keyword=asperopterin en-keyword=glycosylation kn-keyword=glycosylation en-keyword=isoxanthopterin kn-keyword=isoxanthopterin en-keyword=protecting groups kn-keyword=protecting groups en-keyword=pterin glycoside kn-keyword=pterin glycoside END start-ver=1.4 cd-journal=joma no-vol=86 cd-vols= no-issue=2 article-no= start-page=1147 end-page=1165 dt-received= dt-revised= dt-accepted= dt-pub-year=2012 dt-pub=20121231 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine en-subtitle= kn-subtitle= en-abstract= kn-abstract=Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29). en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=KawaguchiMasahiro en-aut-sei=Kawaguchi en-aut-mei=Masahiro kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=SumiMasakazu en-aut-sei=Sumi en-aut-mei=Masakazu kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=MakinoKazuo en-aut-sei=Makino en-aut-mei=Kazuo kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=TsukadaKeiko en-aut-sei=Tsukada en-aut-mei=Keiko kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=3 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=4 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=5 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=6 en-affil= kn-affil=Shujitsu Univ, Sch Pharm en-keyword=Phospha-Sugar kn-keyword=Phospha-Sugar en-keyword=N-Acetyl-D-glucosamine kn-keyword=N-Acetyl-D-glucosamine en-keyword=Phosphoryl Group kn-keyword=Phosphoryl Group en-keyword=C-P Bond Formation kn-keyword=C-P Bond Formation en-keyword=Hetero Sugar kn-keyword=Hetero Sugar END start-ver=1.4 cd-journal=joma no-vol=84 cd-vols= no-issue=2 article-no= start-page=801 end-page=813 dt-received= dt-revised= dt-accepted= dt-pub-year=2012 dt-pub=20120101 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key precursor, N-2-(N,N-dimethylaminomethylene)-6-hydroxymethy1-8-methyl-3[2-(4-nitrophenypethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylam1no-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5-tri-O-benzoy1-beta-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=EjiriKazumasa en-aut-sei=Ejiri en-aut-mei=Kazumasa kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=3 en-affil= kn-affil=Shujitsu Univ, Sch Pharm en-keyword=Isoxanthopterin Glycoside kn-keyword=Isoxanthopterin Glycoside en-keyword=Glycosylation kn-keyword=Glycosylation en-keyword=Pteridine kn-keyword=Pteridine en-keyword=Hydroxymethylation kn-keyword=Hydroxymethylation en-keyword=Protecting Group kn-keyword=Protecting Group END start-ver=1.4 cd-journal=joma no-vol=82 cd-vols= no-issue=2 article-no= start-page=1675 end-page=1683 dt-received= dt-revised= dt-accepted= dt-pub-year=2011 dt-pub=20110301 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=An Efficient Synthesis of Antibiotic SF-2312 (3-Dihydroxyphosphoryl-1,5-dihydroxy-2-pyrrolidone) en-subtitle= kn-subtitle= en-abstract= kn-abstract=N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=ItohChika en-aut-sei=Itoh en-aut-mei=Chika kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= affil-num=1 en-affil= kn-affil=Graduate School of Natural Science and Technology, Okayama University affil-num=2 en-affil= kn-affil=Graduate School of Natural Science and Technology, Okayama University en-keyword=Phosphonic Acid kn-keyword=Phosphonic Acid en-keyword=Hydroxamic Acid kn-keyword=Hydroxamic Acid en-keyword=Antibiotic kn-keyword=Antibiotic en-keyword=2-Pyrrolidone kn-keyword=2-Pyrrolidone en-keyword=C-P Bond kn-keyword=C-P Bond END start-ver=1.4 cd-journal=joma no-vol=21 cd-vols= no-issue=3 article-no= start-page=79 end-page=83 dt-received= dt-revised= dt-accepted= dt-pub-year=2010 dt-pub=201009 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of a Natural Neopterin Glycoside: 3'-O-(-D-Glucopyranosyluronic acid)neopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=1',2'-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]neopterin (1) was prepared from neopterin in 5 steps. Glycosylation of 1 with methyl 2,3,4-tri-O-benzoyl--D-glucopyranosyluronate bromide in the presence of silver triflate and tetramethylurea afforded the corresponding 3'-O-(methyl -D-glucopyranosyluronate) neopterin derivative (2) in 64% yield. The first synthesis of 3'-O-(-D-glucopyranosyluronic acid)neopterin was achieved by successive removal (4 steps) of the protecting groups of 2. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=HattoriTakafumi en-aut-sei=Hattori en-aut-mei=Takafumi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=TakayamaDaisuke en-aut-sei=Takayama en-aut-mei=Daisuke kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=neopterin glycoside kn-keyword=neopterin glycoside en-keyword=D-glucronic acid kn-keyword=D-glucronic acid en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END start-ver=1.4 cd-journal=joma no-vol=80 cd-vols= no-issue=2 article-no= start-page=1013 end-page=1025 dt-received= dt-revised= dt-accepted= dt-pub-year=2010 dt-pub=20100301 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Synthesis of 6-Hydroxymethylpterin - and -D-Glucosides en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key precursor, N(2)-(N,N-dimethylaminomethylene)-6-hydroxymethyl-3-[2-(4-nitrophenyl)ethyl]pterin (11) was efficiently prepared from 2,5,6-triamino-4-hydroxypyrimidine (8) in 5 steps. The first, unequivocal synthesis of 6-hydroxymethylpterin -D-glucoside (6a) was achieved by treatment of 11 with 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)--D-glucopyranosyl bromide (16) in the presence of tetraethylammonium bromide and N-ethyldiisopropylamine, followed by removal of the protecting groups, while 6-hydroxymethylpterin -D-glucoside (6b) was prepared by means of selective glycosylation of 11 with 2,3,4,6-tetra-O-benzoyl--D-glucopyranosyl bromide (12) in the presence of silver triflate and tetramethylurea. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=BabaHiroki en-aut-sei=Baba en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=EjiriKazumasa en-aut-sei=Ejiri en-aut-mei=Kazumasa kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=Pterin Glycoside kn-keyword=Pterin Glycoside en-keyword=Selective Glycosylation kn-keyword=Selective Glycosylation en-keyword=Pteridine kn-keyword=Pteridine en-keyword=Glucopyranosyl Bromide kn-keyword=Glucopyranosyl Bromide en-keyword=Protecting Group kn-keyword=Protecting Group END start-ver=1.4 cd-journal=joma no-vol=20 cd-vols= no-issue=Special Issue article-no= start-page=36 end-page=41 dt-received= dt-revised= dt-accepted= dt-pub-year=2009 dt-pub=200912 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of a Representative, Natural Pterin Glycoside: 2f-O-(-D-Glucopyranosyl)biopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=Glycosylation of N(2)-(N,N-dimethylaminomethylene)-1f-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl) ethyl]biopterin (14) with the novel donor 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)--D-glucopyranosyl bromide (19) in the presence of silver triflate and tetramethylurea predominantly afforded the corresponding -D-glucopyranoside (20a), from which 2f-O-(-D-glucopyranosyl)biopterin (1) was obtained by the successive removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=PfleidererWolfgang en-aut-sei=Pfleiderer en-aut-mei=Wolfgang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=School of Pharmacy, Shujitsu University affil-num=3 en-affil= kn-affil=Fachbereich Chemie, Universit?t Konstanz en-keyword=biopterin D-glucoside kn-keyword=biopterin D-glucoside en-keyword=pterin glycoside kn-keyword=pterin glycoside en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END start-ver=1.4 cd-journal=joma no-vol=65 cd-vols= no-issue=38 article-no= start-page=7989 end-page=7997 dt-received= dt-revised= dt-accepted= dt-pub-year=2009 dt-pub=20090919 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Synthetic studies on pterin glycosides: the first synthesis of 2-O-(-d-glucopyranosyl)biopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=L-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)--d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2-O-(-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=BabaHiroki en-aut-sei=Baba en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=ToyotaHiroki en-aut-sei=Toyota en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=Pterin glycoside kn-keyword=Pterin glycoside en-keyword=Pteridine kn-keyword=Pteridine en-keyword=Glycosylation kn-keyword=Glycosylation en-keyword=Protecting group kn-keyword=Protecting group en-keyword=Total synthesis kn-keyword=Total synthesis END start-ver=1.4 cd-journal=joma no-vol=77 cd-vols= no-issue=2 article-no= start-page=747 end-page=753 dt-received= dt-revised= dt-accepted= dt-pub-year=2009 dt-pub=20090201 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=First Synthesis of Biopterin -D-Glucoside en-subtitle= kn-subtitle= en-abstract= kn-abstract=A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxy-benzyl)--D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2f-O-(-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N(2)-(N,N-dimethylamino- methylene)-1f-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=BabaHiroki en-aut-sei=Baba en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=Pterine Glycoside kn-keyword=Pterine Glycoside en-keyword=Biopterin D-Glucoside kn-keyword=Biopterin D-Glucoside en-keyword=Pteridine kn-keyword=Pteridine en-keyword=Selective -Glycosylation kn-keyword=Selective -Glycosylation en-keyword=Protecting Group kn-keyword=Protecting Group END start-ver=1.4 cd-journal=joma no-vol=76 cd-vols= no-issue=1 article-no= start-page=635 end-page=644 dt-received= dt-revised= dt-accepted= dt-pub-year=2008 dt-pub=20080903 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=An Efficient Synthetic Route for a Versatile Ciliapterin Derivative and the First Ciliapterin D-Mannoside Synthesis en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key precursor, N(2)-(N,N-dimethylaminomethylene)-1f-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]ciliapterin (15) was efficiently prepared from D-xylose via an improved route. The first synthesis of 2f-O-(-D-mannopyranosyl)ciliapterin (2c) was achieved by treatment of 15 with 2,3,4,6-tetra-O-benzoyl--D-mannnopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=BabaHiroki en-aut-sei=Baba en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=KanemotoMitsunori en-aut-sei=Kanemoto en-aut-mei=Mitsunori kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=Pterine Glycoside kn-keyword=Pterine Glycoside en-keyword=Ciliapterin D-Mannoside kn-keyword=Ciliapterin D-Mannoside en-keyword=Pteridine kn-keyword=Pteridine en-keyword=Enol Acetate kn-keyword=Enol Acetate en-keyword=Inversion of Configuration kn-keyword=Inversion of Configuration END start-ver=1.4 cd-journal=joma no-vol=19 cd-vols= no-issue=3 article-no= start-page=72 end-page=78 dt-received= dt-revised= dt-accepted= dt-pub-year=2008 dt-pub=200809 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=An Efficient Synthesis of 2'-O-(-D-Ribofuranosyl)biopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=N(2)-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O (trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl- D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl--D ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=TorigoeKiyoshi en-aut-sei=Torigoe en-aut-mei=Kiyoshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=SoranakaKazuyuki en-aut-sei=Soranaka en-aut-mei=Kazuyuki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=FujitaHiroshi en-aut-sei=Fujita en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=PfleidererWolfgang en-aut-sei=Pfleiderer en-aut-mei=Wolfgang kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=5 en-affil= kn-affil=School of Pharmacy, Shujitsu University affil-num=6 en-affil= kn-affil=Fachbereich Chemie, Universit?t Konstanz en-keyword=biopterin D-riboside kn-keyword=biopterin D-riboside en-keyword=pterin glycoside kn-keyword=pterin glycoside en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting groups kn-keyword=protecting groups END start-ver=1.4 cd-journal=joma no-vol=64 cd-vols= no-issue=9 article-no= start-page=2090 end-page=2100 dt-received= dt-revised= dt-accepted= dt-pub-year=2008 dt-pub=20080225 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin en-subtitle= kn-subtitle= en-abstract= kn-abstract=The key, versatile precursors N-2-(N,N-dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from D-xylose (in 14 steps) and L-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=BabaHiroki en-aut-sei=Baba en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=ToyotaHiroki en-aut-sei=Toyota en-aut-mei=Hiroki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=4 en-affil= kn-affil=School of Pharmacy, Shujitsu University en-keyword=pteridine kn-keyword=pteridine en-keyword=pterin glycoside kn-keyword=pterin glycoside en-keyword=glycosylation kn-keyword=glycosylation en-keyword=protecting group kn-keyword=protecting group END start-ver=1.4 cd-journal=joma no-vol=74 cd-vols= no-issue=1 article-no= start-page=983 end-page=989 dt-received= dt-revised= dt-accepted= dt-pub-year=2007 dt-pub=20071231 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=An Efficient, One-Pot Synthesis of Fosfomycin Dialkyl Esters from (R)-2-Tosyloxypropanal en-subtitle= kn-subtitle= en-abstract= kn-abstract=(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=NakamuraYuichi en-aut-sei=Nakamura en-aut-mei=Yuichi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=2 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University affil-num=3 en-affil= kn-affil=Department of Chemistry, Faculty of Science, Okayama University en-keyword=Fosfomycin kn-keyword=Fosfomycin en-keyword=Epoxidation kn-keyword=Epoxidation en-keyword=C-P Bond Formation kn-keyword=C-P Bond Formation en-keyword=Phosphonate Addition kn-keyword=Phosphonate Addition en-keyword=Diastereoselectivity kn-keyword=Diastereoselectivity END start-ver=1.4 cd-journal=joma no-vol=73 cd-vols= no-issue=1 article-no= start-page=581 end-page=591 dt-received= dt-revised= dt-accepted= dt-pub-year=2007 dt-pub=200712 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=Improved syntheses of D-ribo- and 2-deoxy-D-ribofuranose phospho sugars from methyl -D-ribopyranoside en-subtitle= kn-subtitle= en-abstract= kn-abstract=Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-beta-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-beta-D-erythro-pentopyranoside (20) were efficiently prepared respectively from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside (7a) and its 3,4-O-isopropylidene isomer (7b) in appreciably improved total yields compared with those via previously reported routes. Compounds (12a, 20) were led to D-ribofuranose and 2-deoxy-D-ribofuranose phospho sugars (4, 5). en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=KogaYuko en-aut-sei=Koga en-aut-mei=Yuko kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=KawamotoHeizan en-aut-sei=Kawamoto en-aut-mei=Heizan kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=3 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=4 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem en-keyword=D-ribofuranose phospho sugar kn-keyword=D-ribofuranose phospho sugar en-keyword=2-deoxy-D-ribofuranose analog kn-keyword=2-deoxy-D-ribofuranose analog en-keyword=C-P bond formation kn-keyword=C-P bond formation en-keyword=stannylene acetal kn-keyword=stannylene acetal END start-ver=1.4 cd-journal=joma no-vol=72 cd-vols= no-issue=1 article-no= start-page=411 end-page=420 dt-received= dt-revised= dt-accepted= dt-pub-year=2007 dt-pub=20070413 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=A New Route for Preparation of 2-Deoxy-D-ribofuranose Phospho Sugar en-subtitle= kn-subtitle= en-abstract= kn-abstract=The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tertbutyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxyphosphinoyl-2,4-O-ethylidene-D-erythritol (13a). Elongation of carbon skeleton of the D-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-alpha,beta-D-erythropentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=TsukuiHiroyuki en-aut-sei=Tsukui en-aut-mei=Hiroyuki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=IgiNaomi en-aut-sei=Igi en-aut-mei=Naomi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= en-aut-name=NoguchiAyashi en-aut-sei=Noguchi en-aut-mei=Ayashi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=4 ORCID= en-aut-name=KawamotoHeizan en-aut-sei=Kawamoto en-aut-mei=Heizan kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=5 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=6 ORCID= affil-num=1 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=2 en-affil= kn-affil= affil-num=3 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=4 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=5 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem affil-num=6 en-affil= kn-affil=Okayama Univ, Fac Sci, Dept Chem END start-ver=1.4 cd-journal=joma no-vol=71 cd-vols= no-issue=3 article-no= start-page=517 end-page=522 dt-received= dt-revised= dt-accepted= dt-pub-year=2007 dt-pub=200704 dt-online= en-article= kn-article= en-subject= kn-subject= en-title= kn-title=The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene--D-fructofuranoside as a Key Intermediate en-subtitle= kn-subtitle= en-abstract= kn-abstract=Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene--D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative. en-copyright= kn-copyright= en-aut-name=HanayaTadashi en-aut-sei=Hanaya en-aut-mei=Tadashi kn-aut-name=ԒJ kn-aut-sei=ԒJ kn-aut-mei= aut-affil-num=1 ORCID= en-aut-name=SatoNobuaki en-aut-sei=Sato en-aut-mei=Nobuaki kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=2 ORCID= en-aut-name=YamamotoHiroshi en-aut-sei=Yamamoto en-aut-mei=Hiroshi kn-aut-name= kn-aut-sei= kn-aut-mei= aut-affil-num=3 ORCID= affil-num=1 en-affil= kn-affil=SwEwx@\ affil-num=2 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= affil-num=3 en-affil=Department of Chemistry, Faculty of Science, Okayama University kn-affil= END start-ver=1.4 cd-journal=joma no-vol= cd-vols= no-issue= article-no= start-page= end-page= dt-received= dt-revised= dt-accepted= dt-pub-year=1990 dt-pub=19900328 dt-online= en-article= kn-article= en-subject= kn-subject= en-title=“ɃqL铜ގ̂̍I kn-title=Synthetic Studies of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring en-subtitle= kn-subtitle= en-abstract= kn-abstract= en-copyright= kn-copyright= en-aut-name= en-aut-sei= en-aut-mei= kn-aut-name=ԒJ kn-aut-sei=ԒJ kn-aut-mei= aut-affil-num=1 ORCID= affil-num=1 en-affil= kn-affil=Rw END