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 journalArticle

16 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 languageEnglish
Pages (from-to)8780-8788
Number of pages9
JournalTetrahedron
Volume64
Issue number37
DOIs
Publication statusPublished - Sep 8 2008
Externally publishedYes

Keywords

  • Carbamate
  • Carbohydrate
  • Rearrangement
  • Stereospecific synthesis
  • Urea

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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