Synthetic Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM3 and GM4 Analogs Containing 2- OR 3-Branched Fatty-Alkyl Residues in Place of Ceramide
Synthetic Studies on Sialoglycoconjugates 88: Synthesis of Ganglioside GM3 and GM4 Analogs Containing 2- OR 3-Branched Fatty-Alkyl Residues in Place of Ceramide
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唾液酸糖缀合物 88 的合成研究：含有 2-或 3-支链脂肪烷基残基代替神经酰胺的神经节苷脂 GM3 和 GM4 类似物的合成
DOI：
10.1080/07328309608005679
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发表时间：
1996
影响因子：
1
通讯作者：
M. Kiso
中科院分区：
文献类型：
--
作者：
A. Hasegawa;N. Suzuki;H. Ishida;M. Kiso
摘要合成了4个神经节苷脂GM4和GM3类似物，分别含有取代神经酰胺的2-或3-支链脂肪烷基残基。O-(甲基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三氯乙酰亚胺(13)或O-(甲基5-乙酰氨基-4，7，8，9-tetra-O-acetyl-3，5-dideoxy-D-glycero-α-D-glacto-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三氯乙酰亚胺(14)与2-或3-支链脂肪-烷基-1-醇(9-12)，由相应的支链脂肪酸通过甲酯化和还原得到，用BF3Ot2给出了相应的神经节苷脂类似物(15，17，19，21，23，25，27，29)，通过O-脱酰化和脱酯反应转化为标题化合物。
ABSTRACT 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-glacto-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 BF3Ot2 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.