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
6163
6170
8
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].
Cipolla, L; Nicotra, F; Vismara, E; Guerrini, M
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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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