Branched-chain thiosugars: Temperature effects in the acetolytic deacetalation of furanose sugars

Article abstract of DOI:10.1016/0008-6215(91)80095-5

The synthesis of the branched-chain thiosugar derivatives 8 and 13 from 1,2-O-isopropylidene-D-xylofuranose is described. The acetolytic cleavage of the acetonide group from 8 and 13 was found to yield products arising from opening of the furanose ring when carried out at low temperatures. These include the novel thiolanes 9 and 17. The desired 1,2-di-O-acetyl furanoses 6 and 14 were obtained when the reaction was performed at higher temperatures.