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ID 10593
Eprint ID
10593
FullText URL
Title Alternative
Solid-phase Synthesis of Oligosaccharides Using Novel Alkyne-type Linkers -Selection of Reactive Sites on the support by Sonogashira Reaction-
Author
Abstract
Two new alkyne-type linkers having alkynylmethyloxy moieties were elaborated for solid-phase synthesis of oligosaccharide. A propargyl glycoside-type linker between a sugar residue and a solid support was formed by the Sonogashira reaction of a propargyl glycoside with polymer-supported iodobenzene. A propargyl ester-type linker was also constructed by the same reaction of a 4-(proparygyloxycarbonyl)benzyl glycoside with the latter. Both linkers are stable against acids such as TFA but can be readily cleaved with this acid after conversion to the corresponding alkyne-cobalt complex by treatment with Co2(CO)8. The latter ester linker is generally advantageous in that mild cleavage liberates a proceed only at spatially reactive sites on the solid support where the reagent accesses readily, so that the subsequent reactions including glycosylation on solid phase proceeded smoothly to result in high total yields of the desired oligosaccharides.
Keywords
oligosaccharides
solid-phase synthesis
carbohydrates
glycosylation
cross-coupling
Published Date
2005-02-01
Publication Title
岡山大学農学部学術報告
Publication Title Alternative
Scientific reports of the Faculty of Agriculture, Okayama University
Volume
volume94
Issue
issue1
Publisher
岡山大学農学部
Publisher Alternative
Faculty of Agriculture,Okayama University
Start Page
81
End Page
84
ISSN
0474-0254
NCID
AN00033029
Content Type
Departmental Bulletin Paper
language
日本語
File Version
publisher
Refereed
False
Eprints Journal Name
srfa