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.
Articolo in rivista - Articolo scientifico
glyceroglycolipids; C-glycosides, carbohydrate mimics
English
1997
53
17
6163
6170
none
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].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/31750
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