Synthesis of the trisaccharide segment of phenolic glycolipid from mycobacterium tuberculosis (strain Canetti)

Abstract

The trisaccharide, 2,3,4-(OMe)3-alpha-L-Fucp-(1->3)-a- L-Rhap-(1->3)-2-O-Me-alpha(1, R=lipid), was the phenolic glycolipid fraction of Mycobacterium tuberculosis (strain Canetti). The synthesis of this trisaccharide (2) as methyl ether has been described. The critical 0-glycosylation reaction has been carried out with 1-0-acetylhexoses, promoted by borontrifluoride-etherate to  provide a high degree of alpha-selectivity.