Aryl and arylmethyl C-glycosides through desulfitative stille and carbonylative stille cross-coupling of tinglycals and sulfonyl chlorides

被引:55
作者
Dubbaka, SR [1 ]
Steunenberg, P [1 ]
Vogel, P [1 ]
机构
[1] Swiss Fed Inst Technol, EPFL, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland
关键词
sulfonyl chlorides; tinglycals; C-glycosides; cross-coupling; catalysis; palladium;
D O I
10.1055/s-2004-825587
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed cross-coupling of tinglucal and tingalactal derivatives with arenesulfonyl chlorides provides aryl C-glycoside precursors. Desulfitative carbonylative Stille cross-coupling between 1-naphthalenesulfonyl chloride and a tinglucal derivative gives, after stereoselective reduction of the keto moiety and stereoselective oxidative hydroboration, a protected form of 1-[(1S)-2,6-anhydro-L-glycero-D-gulo-heptitol-1-C-yl] naphthalene [beta-C-glucopyranoside of (S)-(naphtha-1-yl)methanol]. Benzyl C-glycoside precursors are obtained by desulfitative Stille coupling of phenylmethanesulfonyl chloride with the corresponding protected tinglycals.
引用
收藏
页码:1235 / 1238
页数:4
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