76227-37-7

Upstream product

• 76234-88-3 Thioacetic acid S-[(2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethyl] ester 
• 65751-66-8 3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol 
• 76227-34-4 Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester 
• 76227-35-5 [(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-yl]-methanethiol 

Downstream Products

• 76227-38-8 bis-<3-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl)-1,2-di-O-hexadecanoyl-L-glycerol>-6,6-disulphide 

Relevant 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'

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'.