Regioselective glycosylation of 4,6-O-benzylidenated glucopyranosides.
Regioselective glycosylation with allyl 4,6-O-benzylidene-alpha,beta-D-glucopyranoside or methyl 4,6-O-benzylidene-alpha,beta-D-glucopyranoside as the acceptor was investigated. It was found that the regioselectivity depends upon donor size and anomeric configuration of the acceptor, i.e., with a monosaccharide donor and an alpha-form acceptor, the (1-->3)-linked product was obtained predominantly or exclusively, while with disaccharide or trisaccharide donors and either an alpha or beta form acceptor, the (1-->2)-linked oligosaccharides were the only products.
Zeng
Ying
Y
Research Center for Eco-Environmental Sciences, Academia Sinica, Chinese Academy of Sciences, P.O. Box 2871, Beijing 100085, China.
Kong
Fanzuo
F
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D008969:Molecular Sequence Data
D006027:Glycosides