Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

Kazunobu Toshima, Goh Matsuo, Toru Ishizuka, Yasunobu Ushiki, Masaya Nakata, Shuichi Matsumura

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl β-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl α-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.

Original languageEnglish
Pages (from-to)2307-2313
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number7
DOIs
Publication statusPublished - 1998 Apr 3

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Toshima, K., Matsuo, G., Ishizuka, T., Ushiki, Y., Nakata, M., & Matsumura, S. (1998). Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars. Journal of Organic Chemistry, 63(7), 2307-2313. https://doi.org/10.1021/jo972146v