An efficient glycosidation method using 2,3-unsaturated glycosyl donors

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

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13 Citations (Scopus)

Abstract

A novel class of 'armed' glycosyl donors containing a double bond at the C-2 position was designed by mimicking the mechanism of lysozyme-initiated hydrolysis. These donors were used to achieve chemoselective glycosidation of hex-2-enopyranosyl acetate and hexopyranosyl acetate, and synthesis of O-glycosidic linkages between highly deoxygenated sugars and tertiary alcohols.

Original languageEnglish
Pages (from-to)9039-9043
Number of pages5
JournalTetrahedron Letters
Volume47
Issue number51
DOIs
Publication statusPublished - 2006 Dec 18

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Keywords

  • Carbohydrates
  • Chemoselectivity
  • Deoxy sugar
  • Glycosidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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