Tetrahedron p. 4557 - 4566 (1985)
Update date:2022-08-04
Topics: Synthesis Application Experimental Tetraisopropyldisiloxane-1,3-diyl (tips) protecting group Sugar chemistry
Boeckel, C. A. A. van
Visser, G. M.
Boom, J. H. van
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.
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(1958)