Isochromane “versus” O-glycoside synthesis. A study of the reaction of 2-alkoxy-2-fluoro-glycosyl fluorides with alcohols.

作者: Raouf Echarri , Ma Isabel Matheu , Sergio Castillón

DOI: 10.1016/S0040-4020(01)85378-3

关键词: ChemistryBenzyl alcoholAldoseGlycosylFluoridePrimary alcoholOrganic chemistryAlkoxy groupAlcoholReaction mechanism

摘要: Abstract 2-alkoxy-2-fluoro-glycosyl fluorides 1a and 1b react with benzyl alcohol derivatives in the presence of fluorine activating system Cp2HfCl2/AgClO4 giving isochromane or O-glycosides depending on glycosyl fluoride/alcohol ratio. A mechanism consecutive reactions leading to is proposed.

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