An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars

Kazunobu Toshima, Goh Matsuo, Masaya Nakata

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).

Original languageEnglish
Pages (from-to)997-998
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number8
DOIs
Publication statusPublished - 1994

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Glycosides
Sugars
Naphthol
Naphthols
Phenol
Phenols
Derivatives
C-glycoside

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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abstract = "Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).",
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AB - Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25-27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides in high yields (TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).

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