1,2-MONO-, 1,2:3,5-DI-, AND 1,2:5,6-DI-O-ISOPROPYLIDENE-β-L-IDOFURANOSES; AN EXAMPLE OF 1,3-DIOXOLANE-1,3-DIOXANE ISOMERISATION

Article abstract of DOI:10.1016/S0008-6215(00)81002-2

Simple preparative routes to 1,2-O-isopropylidene- and 1,2:5,6-di-O-isopropylideneβ-L-idofuranoses are described.The 1,2:5,6-diacetal is the kinetic product of the reaction of 1,2-O-isopropylidene-β-L-idofuranose with acetone and 2,2-dimethoxypropane in the presence of toluene-p-sulphonic acid but, during longer reaction times, isomerisation to 1,2:3,5-di-O-siopropylidene-β-L-idofuranose occurs, resulting in a approximately equal mixture of the two diacetals.