76227-39-9Relevant academic research and scientific papers
Synthesis of 3-O-(6-Deoxy-6-sulpho-α-D-glucopyranosyl)-1,2-di-O-hexadecanoyl-L-glycerol, 'Sulphoquinovosyl Diglyceride'
Gigg, Roy,Penglis, Anna A. E.,Conant, Robert
, p. 2490 - 2493 (2007/10/02)
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--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'.
