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=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=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=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=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=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=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