Synlett

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

SR Dubbaka, P Steunenberg, P Vogel

Index: Dubbaka, Srinivas Reddy; Steunenberg, Peter; Vogel, Pierre Synlett, 2004 , # 7 p. 1235 - 1238

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Citation Number: 31

Abstract

Abstract 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] ...