Stable C-glycosidic an analogues of 2-O-(beta-D-glucopyranosyl)-sn-glycerol (In), 2-O-(beta-D-galactopyranosyl)-sn glycerol (Ib), 1-O-(beta-D-glucopyranosyl)-sn-glycerol (7) and their dipalmitoyl ester have been synthesised starting from the corresponding 2,3,4,6-tetra-O-benzyl-glyconolactones 9. The 2-O-derivatives 1 were obtained by methylenation of the lactone 9, reaction of the obtained glycoexoenitol 10 with a malonyl radical, reduction of the malonyl derivative 11 and deprotection. The 1-O-derivative 7 was obtained by reaction of the lactone 9 with butenylmagnesium bromide, reduction of the obtained lactol 14, osmylation and deprotection. (C) 1997 Elsevier Science Ltd.
Cipolla, L., Nicotra, F., Vismara, E., Guerrini, M. (1997). Synthesis of stable analogues of glyceroglycolipids. TETRAHEDRON, 53(17), 6163-6170 [10.1016/S0040-4020(97)00273-1].
Synthesis of stable analogues of glyceroglycolipids
CIPOLLA, LAURA FRANCESCA;NICOTRA, FRANCESCO;
1997
Abstract
Stable C-glycosidic an analogues of 2-O-(beta-D-glucopyranosyl)-sn-glycerol (In), 2-O-(beta-D-galactopyranosyl)-sn glycerol (Ib), 1-O-(beta-D-glucopyranosyl)-sn-glycerol (7) and their dipalmitoyl ester have been synthesised starting from the corresponding 2,3,4,6-tetra-O-benzyl-glyconolactones 9. The 2-O-derivatives 1 were obtained by methylenation of the lactone 9, reaction of the obtained glycoexoenitol 10 with a malonyl radical, reduction of the malonyl derivative 11 and deprotection. The 1-O-derivative 7 was obtained by reaction of the lactone 9 with butenylmagnesium bromide, reduction of the obtained lactol 14, osmylation and deprotection. (C) 1997 Elsevier Science Ltd.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
