Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement

Daisuke Sawada; Shinya Sasayama; Hideyo Takahashi; Shiro Ikegami

doi:10.1016/j.tet.2008.06.089

Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement

Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

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

17 Citations (Scopus)

Abstract

We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl group in glucose as an acceptor has been disclosed. Furthermore, we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule.

Original language	English
Pages (from-to)	8780-8788
Number of pages	9
Journal	Tetrahedron
Volume	64
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2008.06.089
Publication status	Published - Sept 8 2008
Externally published	Yes

Keywords

Carbamate
Carbohydrate
Rearrangement
Stereospecific synthesis
Urea

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.06.089

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title = "Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement",

abstract = "We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl group in glucose as an acceptor has been disclosed. Furthermore, we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule.",

keywords = "Carbamate, Carbohydrate, Rearrangement, Stereospecific synthesis, Urea",

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

note = "Funding Information: This work was partially supported by the Ministry of Education, Culture, Sports, Science, and Technology of Japan and Uehara Memorial Foundation (to D.S.). ",

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T1 - Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement

AU - Sawada, Daisuke

AU - Sasayama, Shinya

AU - Takahashi, Hideyo

AU - Ikegami, Shiro

N1 - Funding Information: This work was partially supported by the Ministry of Education, Culture, Sports, Science, and Technology of Japan and Uehara Memorial Foundation (to D.S.).

PY - 2008/9/8

Y1 - 2008/9/8

N2 - We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl group in glucose as an acceptor has been disclosed. Furthermore, we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule.

AB - We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl group in glucose as an acceptor has been disclosed. Furthermore, we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule.

KW - Carbamate

KW - Carbohydrate

KW - Rearrangement

KW - Stereospecific synthesis

KW - Urea

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DO - 10.1016/j.tet.2008.06.089

M3 - Article

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SN - 0040-4020

VL - 64

SP - 8780

EP - 8788

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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