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Synthesis of 3-O-(6-Deoxy-6-sulpho-α-D-glucopyranosyl)-1,2-di-O-hexadecanoyl-L-glycerol, 'Sulphoquinovosyl Diglyceride'

DOI: 10.1039/P19800002490

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2490 - 2493 (1980)

Update date:2022-08-04

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Authors:

Gigg, RoyGigg, Roy

Penglis, Anna A. E.Penglis, Anna A. E.

Conant, RobertConant, Robert

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Article abstract of DOI:10.1039/P19800002490

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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Product name:bis-<3-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl)-1,2-di-O-hexadecanoyl-L-glycerol>-6,6-disulphide

Cas No:76227-38-8

76227-38-8

R&D Labs maybe for 76227-38-8

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