2-DEOXY-D-arabino-HEXOSE, 2-DEOXY-D-lyxo-HEXOSE, AND THEIR (2R)-2-DEUTERIO ANALOGS

Article abstract of DOI:10.1016/S0008-6215(00)85317-3

A general method for the synthesis of 2-deoxyhexoses is described. 2-Deoxy-D-arabino-hexose and 2-deoxy-D-lyxo-hexose were prepared from D-glucose and D-galactose, respectively, by a route involving reduction of the respective 4,5-O-isopropylidene ketene diethyl dithioacetals with lithium aluminum hydride, followed by removal of the protecting groups.In agreement with the results of earlier studies with ketene dithioacetals of pentose analogs, reduction of the hexose ketene dithioacetals was found to occur both regio- and stereo-specifically.Reduction with lithium aluminum deuteride gave the (2R)-2-deoxy-2-deuterio-hexoses exclusively.