Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides

Masahiko Yamaguchi, Akira Horiguchi, Akira Fukuda, Toru Minami

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

The glycosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosyl fluoride in the presence of BF3OEt2 to give, predominantly, α-anomers has been studied. In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved. The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.

Original languageEnglish
Pages (from-to)1079-1082
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
DOIs
Publication statusPublished - 1990

ASJC Scopus subject areas

  • Chemistry(all)

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