Tetrahedron Letters p. 5469 - 5470 (1995)
Update date:2022-08-16
Topics:
Dillon, Michael P.
Maag, Hans
Muszinsky, Dawn M.
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.
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