Synthesis of 3-O-(6-deoxy-6-sulpho-α-D-glucopyranosyl)-1,2-di-O-hexadecanoyl-L-glycerol, ‘sulphoquinovosyl diglyceride’

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Abstract
3-O-(2,3,4-Tri-O-benzyl-6-O-tosyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol was treated with potassium thioacetate and the product was hydrolysed with base to give the corresponding 6-deoxy-6-thioderivative which on oxidation with iodine gave the crystalline disulphide. The isopropylidene groups were hydrolysed and the product was acylated with hexadecanoyl chloride in pyridine to give crystalline bis-[3-O-(2,3,4tri-O-benzyl-6-deoxy-α-D-glucopyrancsyl)-1,2-di-O-hexadecanoyl-L-glycerol]-6,6-disulphide. Oxidation of this compound with 3-chloroperbenzoic acid and subsequent hydrogenolysis of the benzyl groups gave the title compound with properties similar to those of a sample prepared by hydrogenation of the natural ‘sulphoquinovosyl diglyceride.’

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