Journal of the Chemical Society. Perkin transactions I p. 2490 - 2493 (1980)
Update date:2022-08-04
Topics:
Gigg, Roy
Penglis, Anna A. E.
Conant, Robert
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-(2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl)-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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