摘要
报道了α-Neu5Ac-(2-3)-β-Gal-(1-4)-β-Glc-(1-1)-Cer(GM3)的有效合成方法.将选择性保护的乳糖二醇与唾液酸黄原酸酯(Xanthate)在AgOTf/PhSCl催化下高立体、高区域选择性糖苷化得到含唾液酸的三糖,经脱苄基保护及全乙酰化后,在温和条件下脱去还原端保护基,并制备成三氯乙酰亚胺酯糖苷,与选择性保护的鞘氨醇缩合得到含叠氮化合物9.后者用Ph3P还原后,在EDC存在下与硬脂酸酰化反应,得化合物11,脱去保护基后获得目标产物GM3(1),为研究肿瘤疫苗提供有用材料.化合物结构经NMR,MS和HRMS确证.
An efficient synthesis of α-Neu5Ac-（2-3）-β-Gal-（1-4）-β-Glc-（1-1）-Cer （GM3） was described. A suitably protected lactoside diol was glycosylated with sialyl xanthate to give only the α-sialyl trisaccharide in good yield based on a highly stereoand regioselective sialylation. Condensation of the azidosphingosine 8 with the imidate 7 using a promoter TMSOTf, afforded the glycolipid 9, which was directly transformed to 10 by reduction with Ph3P and subsequent acylation with octadecanoic acid in the presence of EDC. After deprotection, the target GM3 was afforded, which can be applied to study of the tumor-vaccine. The struc- tures of these compounds were fully confirmed by XH and X3C NMR, mass spectra （MS） and HRMS.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
2007年第24期2909-2916,共8页
Acta Chimica Sinica
基金
人事部中国博士后科研基金(No.20060400709)
天津科技大学基金(No.20060403)资助项目.
