A Novel Approach to the Synthesis of C-Glycosyl Compounds: The Wittig Rearrangement

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Abstract
Partially protected benzyl α-and β-pyranosides undergo Wittig rearrangement reactions on treatment with strong bases in tetrahydrofuran to give hydroxymethylphenyl C-glycosyl derivatives. Two products were generally obtained and all Wittig rearrangement products retained the configuration at the migrating anomeric center. In benzene, benzyl 4,6-O-isopropylidene-β-D-glucopyranoside reacted with n-butyl lithium to give addition to the anomeric center accompanied by ring opening with loss of the aglycone. Allyl glycosides do not give Wittig rearrangement products.