The Regioselective Opening of 5-O-Benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose With Organostannanes

Article abstract of DOI:10.1016/00404-0399(50)1057O-

The trimethylsilyl triflate mediated regioselective opening of 5-O-benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose with organostannanes is presented.Hydrolysis of the initially formed 1-O-trimethylsilyl ether yields the products of S- and C-glycosidation with predominantly β-stereochemistry in good yields.The unusual addition of acetonitrile to the intermediate oxonium ion when the reaction is performed in this medium is also outlined.