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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (12): 1355-1362. 上一篇    下一篇

研究论文

以N-乙酰基-5-N,4-O-噁唑烷酮保护的唾液酸对甲基苯硫苷给体合成神经节苷脂GM3三糖甲苷衍生物

陈 力a 梁芬芬a 许美凤a,b 邢国文*,a 邓志威b

  

  1. (a北京师范大学化学学院 北京 100875)
    (b北京师范大学分析测试中心 北京 100875)

  • 投稿日期:2008-11-05 修回日期:2009-01-12 发布日期:2009-06-28
  • 通讯作者: 邢国文

Synthesis of the Methyl Glycoside of Ganglioside GM3 Trisaccharide Derivative with N-Acetyl-5-N,4-O-Oxazolidinone Protected p-Toluenethiosialoside

Chen, Li a Liang, Fenfen a Xu, Meifeng a,b Xing, Guowen *,a Deng, Zhiwei b

  

  1. (a Department of Chemistry, Beijing Normal University, Beijing 100875)
    (bAnalytical and Testing Center, Beijing Normal University, Beijing 100875)
  • Received:2008-11-05 Revised:2009-01-12 Published:2009-06-28
  • Contact: XING Guo-Wen

PDF

1756

被引次数

5

详细研究了N-乙酰基-5-N,4-O-噁唑烷酮保护的唾液酸对甲基苯硫苷给体1与四种苄基或苯甲酰基保护的半乳糖甲苷二醇的唾液酸化反应, 以较高的产率(72%～89%)得到了相应的唾液酸化产物, α/β＝(1.6～2.0)∶1. 在此基础上, 以乳糖为原料通过7步反应以19%的总产率制得了2,3,6,2’,6’-五-O-苯甲酰基-β-乳糖甲苷17, 使用唾液酸给体1将化合物17唾液酸化, 成功地得到神经节苷脂GM3三糖甲苷衍生物18, 产率68%, α/β＝1.6∶1.

关键词: 唾液酸, 神经节苷脂GM3, 糖苷化, 噁唑烷酮

The coupling reaction of N-acetyl-5-N,4-O-oxazolidinone protected p-toluenethiosialoside 1, with four kinds of benzyl or benzoyl protected methyl galactoside diols was deeply studied, which showed α-selectivity with α/β＝1.6～2.0 and afforded the corresponding sialylation products in high yields (72%～89%). Based on these results, a methyl 2,3,6,2’,6’-penta-O-benzyl-β-lactoside 17 was prepared from lactose with 7 steps in a 19% total yield. Sialylation of compound 17 with donor 1 successfully produced the methyl glycoside ganglioside GM3 trisaccharide derivative in a 68% yield and α/β＝1.6∶1.

Key words: sialic acid, ganglioside GM3, glycosylation, oxazolidinone