SYNTHESIS OF PHOSPHATIDYL-β-GLUCOSYL GLYCEROL CONTAINING A DIOLEOLYL DIGLYCERIDE MOIETY. APPLICATION OF THE TETRAISOPROPYLDISILOXANE-1,3-DIYL (TIPS) PROTECTING GROUP IN SUGAR CHEMISTRY. PART IV

Article abstract of DOI:10.1016/S0040-4020(01)82350-4

The preparation of phosphatidyl-β-glucosyl diglyceride 12c is described.The synthesis of glycophospholipid 12c was accomplished by using: (a) the levulinoyl group for the temporary protection of the glucose hydroxyl functions of 6b, which could then be converted into the dioleoyl substituted derivative 7c; (b) the tetraisopropyldisiloxane-1,3-diyl (TIPS) group to protect the 3'- and 4'-hydroxyl groups of 7c, in a two step procedure, to afford compound 8; (c) a 2,4-dichlorophenyl protected phosphatidic acid derivative 11.Compound 11 could be selectively coupled to the primary hydroxyl function of 8 to afford the fully protected glycophospholipid 12a.Finally, removal of the 2,4-dichlorophenyl and TIPS protecting groups from 12a was performed with syn-4-nitrobenzaldoximate and fluoride ions, respectively, to afford glycophospholipid 12c.