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J Org Chem ; 80(17): 8501-10, 2015 Sep 04.
Article in English | MEDLINE | ID: mdl-26292956

ABSTRACT

Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.


Subject(s)
Boron Compounds/chemistry , Caryophyllaceae/chemistry , Oligosaccharides/chemical synthesis , Saponins/chemistry , Carbohydrate Sequence , Glycosylation , Oligosaccharides/chemistry
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