Carbohydrate research

Palladium (0)-assisted synthesis of C-glycopyranosyl compounds

LV Dunkerton, JM Euske, AJ Serino

Index: Dunkerton, Lois V.; Euske, Jack M.; Serino, Anthony J. Carbohydrate Research, 1987 , vol. 171, p. 89 - 108

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Citation Number: 48

Abstract

Abstract Tetrakis (triphenylphosphine) palladium (0) effects the regio-and stereo-selective alkylation of 2-acetoxy-5, 6-dihydro-2H-pyrans and 1-S-acetyl-1-thiohex-2-enopyranosides. Use of stabilized carbanions resulted in the formation of alkylated dihydropyrans with net retention at the oxygen-bearing carbon atom. Examples include the preparation of2- [acetamidobis (ethoxycarbonyl) methyl]-5, 6-dihydro-2H-pyran, 2-[acetamidobis ( ...