Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars

Takashi Yamanoi, Ryo Inoue, Sho Matsuda, Keita Hamasaki

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.

Original languageEnglish
Pages (from-to)30-33
Number of pages4
JournalLetters in Organic Chemistry
Volume5
Issue number1
DOIs
Publication statusPublished - 2008 Jan

Fingerprint

Bismuth
Sugars
Glycosides
Methylene Chloride
Alcohols

Keywords

  • 1,1'-disaccharide
  • 1-hydroxy sugar
  • Bismuth(III) triflate
  • Glycosidation
  • Glycoside

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars. / Yamanoi, Takashi; Inoue, Ryo; Matsuda, Sho; Hamasaki, Keita.

In: Letters in Organic Chemistry, Vol. 5, No. 1, 01.2008, p. 30-33.

Research output: Contribution to journalArticle

Yamanoi, Takashi ; Inoue, Ryo ; Matsuda, Sho ; Hamasaki, Keita. / Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars. In: Letters in Organic Chemistry. 2008 ; Vol. 5, No. 1. pp. 30-33.
@article{a3766f1d4af44dc6a15a189c9084642e,
title = "Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars",
abstract = "This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol{\%} bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.",
keywords = "1,1'-disaccharide, 1-hydroxy sugar, Bismuth(III) triflate, Glycosidation, Glycoside",
author = "Takashi Yamanoi and Ryo Inoue and Sho Matsuda and Keita Hamasaki",
year = "2008",
month = "1",
doi = "10.2174/157017808783330289",
language = "English",
volume = "5",
pages = "30--33",
journal = "Letters in Organic Chemistry",
issn = "1570-1786",
publisher = "Bentham Science Publishers B.V.",
number = "1",

}

TY - JOUR

T1 - Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars

AU - Yamanoi, Takashi

AU - Inoue, Ryo

AU - Matsuda, Sho

AU - Hamasaki, Keita

PY - 2008/1

Y1 - 2008/1

N2 - This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.

AB - This paper describes the O-glycoside formation from 1-hydroxy sugars by the bismuth(III) triflate-catalyzed dehydrative glycosidation. The reactions of the 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux for 15 min in dichloromethane afforded the O-glycosides in good yields. This paper clarifies several important properties during the bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars.

KW - 1,1'-disaccharide

KW - 1-hydroxy sugar

KW - Bismuth(III) triflate

KW - Glycosidation

KW - Glycoside

UR - http://www.scopus.com/inward/record.url?scp=38949216070&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=38949216070&partnerID=8YFLogxK

U2 - 10.2174/157017808783330289

DO - 10.2174/157017808783330289

M3 - Article

AN - SCOPUS:38949216070

VL - 5

SP - 30

EP - 33

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

SN - 1570-1786

IS - 1

ER -