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]naphthalene [β-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.
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