The brθnsted acid-catalyzed O-glycosidation of 1-C-alkyl-D-glucopyranose derivatives

Takashi Yamanoi; Sho Matsuda; Ippo Yamazaki; Ryo Inoue; Keita Hamasaki; Mikio Watanabe

doi:10.3987/COM-06-10684

The brθnsted acid-catalyzed O-glycosidation of 1-C-alkyl-D-glucopyranose derivatives

Takashi Yamanoi, Sho Matsuda, Ippo Yamazaki, Ryo Inoue, Keita Hamasaki, Mikio Watanabe

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.{A figure is presented}.

Original language	English
Pages (from-to)	673-677
Number of pages	5
Journal	Heterocycles
Volume	68
Issue number	4
DOIs	https://doi.org/10.3987/COM-06-10684
Publication status	Published - 2006 Apr 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.{A figure is presented}.",

author = "Takashi Yamanoi and Sho Matsuda and Ippo Yamazaki and Ryo Inoue and Keita Hamasaki and Mikio Watanabe",

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T1 - The brθnsted acid-catalyzed O-glycosidation of 1-C-alkyl-D-glucopyranose derivatives

AU - Yamanoi, Takashi

AU - Matsuda, Sho

AU - Yamazaki, Ippo

AU - Inoue, Ryo

AU - Hamasaki, Keita

AU - Watanabe, Mikio

PY - 2006/4/1

Y1 - 2006/4/1

N2 - We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.{A figure is presented}.

AB - We found that the O-glycosidation between various kinds of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses and alcohols in the presence of 5 mol % of trifluoromethanesulfonic acid or bis(trifluoromethane)sulfonimide stereoselectively produced the corresponding 1-C-alkyl-α-D-glucopyranosides in good yields.{A figure is presented}.

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JF - Heterocycles

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The brθnsted acid-catalyzed O-glycosidation of 1-C-alkyl-D-glucopyranose derivatives

Abstract

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