SYNTHESIS OF TWO PURPLE-MEMBRANE GLYCOLIPIDS AND THE GLYCOLIPID SULFATE O-(β-D-GLUCOPYRANOSYL 3-SULFATE)-(1->6)-O-α-D-MANNOPYRANOSYL-(1->2)-O-α-D-GLUCOPYRANOSYL-(1->1)-2,3-DI-O-PHYTANYL-sn-GLYCEROL

Article abstract of DOI:10.1016/0008-6215(84)85200-3

The two purple-membrane glycolipids O-β-D-glucopyranosyl- and O-β-D-galactopyranosyl-(1->6)-O-α-D-mannopyranosyl-(1->2)-O-α-D-glucopyranosyl-(1->1)-2,3-di-O-phytanyl-sn-glycerol were prepared by coupling O-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->1)-2,3-di-O-phytanyl-sn-glycerol (9) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide or 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide, respectively, followed by deacetylation.The glycolipid sulfate O-(β-D-glucopyranosyl 3-sulfate)-(1->6)-O-α-D-mannopyranosyl-(1->2)-O-α-D-glucopyranosyl-(1->1)-2,3-di-O-phytanyl-sn-glycerol was prepared by coupling of 9 with 2,4,6-tri-O-acetyl-3-O-trichloroethyloxycarbonyl-α-D-glucopyranosyl bromide in the presence of Hg(CN)2/HgBr2 followed by selective removal of the 3"'-trichloroethyloxycarbonyl group, sulfation of HO-3"', and deacetylation.The suitably protected key-intermediate 9 could be prepared by two distinct approaches.