We report the strategy for the stereoselective synthesis of 1,2-trans glycosides in the absence of NGP (neighboring group participation). Present protocol for the selective glycosylation mainly rely on catalyst control rather than protecting group selection. Using this protocol, several glycosides were prepared. Cost effective zinc acetate was found to be the best catalyst that provided desired 1,2-trans glycosides from glucose and mannose derived glycosyl halides at room temperature unlike traditional cryogenic conditions.
The first total synthesis of capsular polysaccharide (CPS) repeating unit [2)-α-l-Rhap-1!P!4-β-d-ManpNAc-(1!4)-α-d-Glcp-(1] n of streptococcus suis serotype 8 is reported. The key features of the synthesis are the formation of 1,2 cis glycosidic linkage between mannosamine and glucose derived monomers to get disaccharide which on coupling with rhamnose Hphosphonate followed by oxidation of PÀ H bond and global debenzylation provide targeted trisaccharide repeating unit of streptococcus suis serotype 8.
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