A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement

Daisuke Sawada; Shinya Sasayama; Hideyo Takahashi; Shiro Ikegami

doi:10.1016/j.tetlet.2006.07.139

A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement

Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

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

30 Citations (Scopus)

Abstract

We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid.

Original language	English
Pages (from-to)	7219-7223
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.139
Publication status	Published - Oct 2 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.07.139

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abstract = "We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid.",

author = "Daisuke Sawada and Shinya Sasayama and Hideyo Takahashi and Shiro Ikegami",

note = "Funding Information: Partial financial support for this research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and Uehara Memorial Foundation to D.S. are gratefully acknowledged. ",

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AU - Sawada, Daisuke

AU - Sasayama, Shinya

AU - Takahashi, Hideyo

AU - Ikegami, Shiro

N1 - Funding Information: Partial financial support for this research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan, and Uehara Memorial Foundation to D.S. are gratefully acknowledged.

PY - 2006/10/2

Y1 - 2006/10/2

N2 - We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid.

AB - We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid.

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JO - Tetrahedron Letters

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ER -

A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement

Abstract

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