The Wittig-cyclization procedure: acid promoted intramolecular formation of 3-C-branched-chain 3,6-anhydro furano sugars via 2'-oxopropylene derivatives.

ABSTRACT

Some olefinic Wittig products, 3-deoxy-5,6-O-isopropylidene-3-C-(2'-oxopropylene)-1,2-O-alkylidene hexofuranose derivatives were converted to the branched-chain 3,6-anhydro-3-C-(2'-oxopropyl) derivatives on treatment with ion exchange resin Amberlite 120 (H(+)) in methanol-water at room temperature. Hydrolysis of 5,6-isopropylidene groups and intramolecular ring-closures took place in one pot reactions.