Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates

Kaname Sasaki, Takayuki Wakamatsu, Shuichi Matsumura, Kazunobu Toshima

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

Original languageEnglish
Pages (from-to)8271-8274
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number47
DOIs
Publication statusPublished - 2006 Nov 20

Keywords

  • Carbohydrates
  • Chemoselectivity
  • Hydrogenation
  • Hydrogenolysis
  • Tetrahydropyrans

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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