An approach to the synthesis of α-(1-6)-C-disaccharides by tandem Tebbe methylenation and Claisen rearrangement

DJ Chambers, GR Evans, AJ Fairbanks

Index: Chambers, David J.; Evans, Graham R.; Fairbanks, Antony J. Tetrahedron, 2005 ,  vol. 61,  # 30  p. 7184 - 7192

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Citation Number: 31

Abstract

Uronic acids, most efficiently synthesised from the corresponding alcohols by two step Dess- Martin and sodium chlorite mediated oxidation, may be used as coupling partners for esterification with an allo glycal as substrates for the tandem Tebbe/Claisen approach to the synthesis of 1-6 linked C-disaccharides. Whilst esters of glucuronic and mannuronic acids successfully undergo Tebbe methylenation, esters derived from galacturonic acids are ...