Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

Masaki Ishihara; Yuka Takagi; Gefei Li; Masato Noguchi; Shin Ichiro Shoda

doi:10.1246/cl.130646

Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

Masaki Ishihara, Yuka Takagi, Gefei Li, Masato Noguchi, Shin Ichiro Shoda

ENG - Biomolecular Engineering

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

6 Citations (Scopus)

Abstract

A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.

Original language	English
Pages (from-to)	1235-1237
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	10
DOIs	https://doi.org/10.1246/cl.130646
Publication status	Published - 2013

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.130646

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abstract = "A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.",

author = "Masaki Ishihara and Yuka Takagi and Gefei Li and Masato Noguchi and Shoda, {Shin Ichiro}",

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T1 - Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

AU - Ishihara, Masaki

AU - Takagi, Yuka

AU - Li, Gefei

AU - Noguchi, Masato

AU - Shoda, Shin Ichiro

PY - 2013

Y1 - 2013

N2 - A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.

AB - A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

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ER -

Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

Abstract

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