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

Fingerprint

Carbamates
Oligosaccharides
Sugars
Urea
Sugar Alcohols
Sugar Acids
Disaccharides
Carboxylic Acids
Hydroxyl Radical
Amines
Glucose
Molecules

Keywords

  • Carbamate
  • Carbohydrate
  • Rearrangement
  • Stereospecific synthesis
  • Urea

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement. / Sawada, Daisuke; Sasayama, Shinya; Takahashi, Hideyo; Ikegami, Shiro.

In: Tetrahedron, Vol. 64, No. 37, 08.09.2008, p. 8780-8788.

Research output: Contribution to journalArticle

Sawada, Daisuke ; Sasayama, Shinya ; Takahashi, Hideyo ; Ikegami, Shiro. / Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement. In: Tetrahedron. 2008 ; Vol. 64, No. 37. pp. 8780-8788.
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