Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

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

研究成果: Article査読

62 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)2307-2313
ページ数7
ジャーナルJournal of Organic Chemistry
63
7
DOI
出版ステータスPublished - 1998 4月 3
外部発表はい

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル