Aryl and Arylmethyl C-Glycosides through Desulfitative Stille and Carbonylative Stille Cross-Coupling of Tinglycals and Sulfonyl Chlorides

Srinivas Reddy Dubbaka; Peter Steunenberg; Pierre Vogel

doi:10.1055/s-2004-825587

LETTER

Aryl and Arylmethyl C-Glycosides through Desulfitative Stille and Carbonylative Stille Cross-Coupling of Tinglycals and Sulfonyl Chlorides

Srinivas Reddy Dubbaka, Peter Steunenberg, Pierre Vogel*
Laboratory of glycochemistry and asymmetric synthesis, Swiss Federal Institute of Technology (EPFL), BCH CH-1015 Lausanne, Switzerland
Fax: +41(21)6939375; e-Mail: pierre.vogel@epfl.ch;

Abstract

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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.

Key words

sulfonyl chlorides - tinglycals - C-glycosides - cross-coupling - catalysis - palladium

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