Novel modes for selective protection of ketose sugars and oligosaccharides of biological and industrial importance

Abstract

2-Methoxypropene converts carbohydrates into cyclic isopropylidene acetals under exclusively kinetic control, affording novel, partially protected sugars of value in synthesis; such disaccharides as maltose and lactose react without glycosidic cleavage to give 4′,6′-acetals (on the non-reducing extremity), and lactose also undergoes inter-residue acetonation between O-2′ and O-6.