Synthetic studies on sialoglycoconjugates 88: Synthesis of ganglioside GM3 and GM4 analogs containing 2- or 3-branched fatty-alkyl residues in place of ceramide

Article abstract of DOI:10.1080/07328309608005679

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.

Full text of DOI:10.1080/07328309608005679

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Synthetic Studies on
Sialoglycoconjugates 88: Synthesis
of Ganglioside GM3 and GM4 Analogs
Containing 2- OR 3-Branched Fatty-Alkyl
Residues in Place of Ceramide
Akira Hasegawa a , Naomi Suzuki a , Hideharu Ishida a & Makoto Kiso
a
a Department of Applied Bioorganic Chemistry , Gifu University ,
Gifu, 501-11, Japan
Published online: 22 Aug 2006.
To cite this article: Akira Hasegawa , Naomi Suzuki , Hideharu Ishida & Makoto Kiso (1996) Synthetic
Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM3 and GM4 Analogs Containing 2- OR
3-Branched Fatty-Alkyl Residues in Place of Ceramide, Journal of Carbohydrate Chemistry, 15:5,
623-637, DOI: 10.1080/07328309608005679
To link to this article: http://dx.doi.org/10.1080/07328309608005679
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