A simplified procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol from L-arabinose.
A new procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol is described. L-arabinose is converted to its 4,5-monoisopropylidene diethyl mercaptal derivative. This compound is then subjected to periodate oxidation and borohydride reduction. Following neutralization, the aceton-glycerol is extracted from the aqueous solution into chloroform. Evaporation of the chloroform and subsequent distillation yielded pure 2,3-O-isopropylidene-sn-glycerol ([alpha]D22 = -14.5 degrees (in substance)) in an overall yield of 15-25%.
D001089:Arabinose; D004148:Dioxolanes / Q000138:chemical synthesis*; D004149:Dioxoles / Q000138:chemical synthesis*; D008722:Methods; D009904:Optical Rotation; D013237:Stereoisomerism
D004148:Dioxolanes; D004149:Dioxoles; C024356:2,2-dimethyl-1,3-dioxolane-4-methanol; D001089:Arabinose