SYNTHESIS OF STABLE ANALOGS OF GLYCEROGLYCOLIPIDS

Stable C-glycosidic an analogues of 2-O-(beta-D-glucopyranosyl)-sn-gly cerol (In), 2-O-(beta-D-galactopyranosyl)-sn glycerol (Ib), 1-O-(beta- D-glucopyranosyl)-sn-glycerol (7) and their dipalmitoyl ester have bee n synthesised starting from the corresponding 2,3,4,6-tetra-O-benzyl-g lyconolactones 9. The 2-O-derivatives 1 were obtained by methylenation of the lactone 9, reaction of the obtained glycoexoenitol 10 with a m alonyl radical, reduction of the malonyl derivative 11 and deprotectio n. The 1-O-derivative 7 was obtained by reaction of the lactone 9 with butenylmagnesium bromide, reduction of the obtained lactol 14, osmyla tion and deprotection. (C) 1997 Elsevier Science Ltd.