An effective sialylation method using N-Troc- and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen
An effective sialylation method using N-Troc- and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen
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DOI：
10.1055/s-2004-817759
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发表时间：
2004-03-09
期刊：
影响因子：
2
通讯作者：
Takahashi, T
中科院分区：
文献类型：
--
作者：
Adachi, M;Tanaka, H;Takahashi, T
我们描述了一种使用带有各种N-保护基团的β-硫代唾液酸苷的有效唾液酸化方法。将β-硫代唾液酸苷的C-5氨基修饰为N-Fmoc和N-Troc衍生物，增强了它们的糖苷化反应活性。此外，适量的MS-3 Angstrom对提高α-连接唾液酸苷的产率是有效的。支化型一锅糖基化引发N-Troc保护的β-硫代苯基唾液酸苷在伯醇中的糖苷化，以良好的产率提供了受保护的2，6-sialyl-T抗原，该抗原被转化为完全去保护的糖基氨基酸。
We describe an efficient sialylation method using beta-thiosialosides with various N-protecting groups. Modification of the C-5 amino group of beta-thiosialosides into N-Fmoc and N-Troc derivatives enhanced their reactivity in glycosidation. In addition, a minimum amount of MS-3 Angstrom was effective to improve the yield of alpha-linked sialoside. Branched type one-pot glycosylation initiating glycosidation of the N-Troc-protected beta-thiophenyl sialoside at a primary alcohol provided the protected 2,6-sialyl-T antigen in good yield, which was converted to the fully deprotected glycosyl amino acid.