Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation

Takashi Yamanoi, Ryo Inoue, Sho Matsuda, Kazuya Iwao, Yoshiki Oda, Akihiro Yoshida, Keita Hamasaki

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1 -hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux temperature for 15 min in dichloromethane afforded O-glycosides in good yields. An 1,6-anhydro-β-D-glucopyranosidic linkage was formed by the intramolecular condensation of the corresponding 1-hydroxy sugar performed with similar reaction conditions using 5 mol% bismuth(III) triflate. A reaction using 10 mol% bismuth(III) triflate at room temperature in dichloromethane promoted the self- or cross-condensations of 1-hydroxy sugars to produce several kinds of 1,1′-disaccharides. This paper reports some important properties of bismuth(III) triflate catalyzed dehydrative glycosidation using 1-hydroxy sugars to form various O-glycosidic linkages.

Original languageEnglish
Pages (from-to)445-460
Number of pages16
JournalHeterocycles
Volume77
Issue number1
DOIs
Publication statusPublished - 2009 Jan 1

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Bismuth
Sugars
Methylene Chloride
Condensation
Condensation reactions
Disaccharides
Glycosides
Alcohols
Temperature

Keywords

  • 1,1′-Disaccharide
  • 1-Hydroxy Sugar
  • Bismuth(III) Triflate
  • Glycosidation
  • Glycoside

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. / Yamanoi, Takashi; Inoue, Ryo; Matsuda, Sho; Iwao, Kazuya; Oda, Yoshiki; Yoshida, Akihiro; Hamasaki, Keita.

In: Heterocycles, Vol. 77, No. 1, 01.01.2009, p. 445-460.

Research output: Contribution to journalArticle

Yamanoi, Takashi ; Inoue, Ryo ; Matsuda, Sho ; Iwao, Kazuya ; Oda, Yoshiki ; Yoshida, Akihiro ; Hamasaki, Keita. / Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. In: Heterocycles. 2009 ; Vol. 77, No. 1. pp. 445-460.
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