Synthesis of phosphatidyl-α-glucosyl glycerol containing a dioleoyl phosphatidyl moiety. Application of the tetraisopropyldisiloxane-1,3-diyl (tips) protecting group in sugar chemistry. part III1 1 For part I and II see references 11 and 39, respectively.

Article abstract of DOI:10.1016/S0040-4020(01)82349-8

In this study we demonstrate that the tetraisopropyldisiloxane-1,3-diyl protecting group could be introduced, in a two step procedure, at the 3'- and 4'-hydroxyl functions of α-glucosyldiglyceride 3 to give derivative 6. Compound 6 could be selectively condensed with a suitably protected phosphatidyl part 9 at its primary hydroxyl function to afford the protected glycophospholipid 10a. The phosphatidyl part 9 was obtained by phosphorylation of optically pure 1,2-di-O-oleoyl-sn-glycerol (8a) with phosphoditriazolide 7b. Finally, the 2,4-dichlorophenyl and TIPS protecting groups were removed from 10a by syn-4-nitro-benzaldoximate and fluoride ions, respectively, to afford glycophospholipid 10c.