180476-40-8Relevant academic research and scientific papers
Synthetic studies on sialoglycoconjugates 88: Synthesis of ganglioside GM3 and GM4 analogs containing 2- or 3-branched fatty-alkyl residues in place of ceramide
Hasegawa, Akira,Suzuki, Naomi,Ishida, Hideharu,Kiso, Makoto
, p. 623 - 637 (2007/10/03)
Each of four ganglioside GM4 and GM3 analogues containing 2- or 3-branched fatty alkyl residues in place of ceramide have been synthesized. Coupling of O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-2,4,6-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate (13) or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-3-O-acetyl-2,4-di-O-benzoyl-α-D- glucopyranosyl trichloroacetimidate (14) with 2- or 3-branched fatty-alkyl-1-ols (9-12), prepared from the corresponding branched fatty acids by methyl esterification and reduction, using BF3·OEt2 gave the corresponding ganglioside analogues (15, 17, 19, 21, 23, 25, 27, 29) in good yields, which were coverted, via O-deacylation and de-esterification, into the title compounds.
