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

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Research output: Contribution to journalArticle

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

Fingerprint

Acetates
Sugar Alcohols
Muramidase
Sugars
Hydrolysis
Alcohols

Keywords

  • Carbohydrates
  • Chemoselectivity
  • Deoxy sugar
  • Glycosidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An efficient glycosidation method using 2,3-unsaturated glycosyl donors. / Sasaki, Kaname; Matsumura, Shuichi; Toshima, Kazunobu.

In: Tetrahedron Letters, Vol. 47, No. 51, 18.12.2006, p. 9039-9043.

Research output: Contribution to journalArticle

Sasaki, Kaname ; Matsumura, Shuichi ; Toshima, Kazunobu. / An efficient glycosidation method using 2,3-unsaturated glycosyl donors. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 51. pp. 9039-9043.
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