95058-05-2Relevant academic research and scientific papers
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
Boeckel, Constant A. A. van,Westerduin, Pieter,Boom, Jacques H. van
, p. 219 - 234 (2007/10/02)
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.
SYNTHESIS OF 2,3-DI-O-PHYTANYL-1-O-6)-MANNOSYL-α(1->2)-GLUCOSYL-α(1->1)>-SN-GLYCEROL. PURPLE MEMBRANE GLYCOLIPIDS
Boeckel, C. A. A. van,Westerduin, P.,Boom, J. H. van
, p. 2819 - 2822 (2007/10/02)
A convenient approach to the synthesis of triglycosyl-2,3-di-O-phytanyl-sn-glycerols will be presented.Special attention will be paid to the use of the following protective groups in carbohydrate chemistry: the 2,2,2-trichloroethoxycarbonyl, the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl and the o-dibromomethyl benzoyl group.
