用于合成α(2→9)寡唾液酸的N-三氟乙酰基亚磷酸唾液酸供体。

N-trifluoroacetyl sialyl phosphite donors for the synthesis of alpha(2 --> 9) oligosialic acids.

作者信息

Lin Chang-Ching, Huang Kuo-Ting, Lin Chun-Cheng

机构信息

Institute of Chemistry and Genomic Research Center, Academia Sinica, Taipei, Taiwan.

出版信息

Org Lett. 2005 Sep 15;7(19):4169-72. doi: 10.1021/ol0515210.

DOI:10.1021/ol0515210

PMID:16146379

Abstract

[reaction: see text] A new method for the synthesis of alpha(2 --> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.

摘要

[反应：见正文] 开发了一种合成α(2→9)寡唾液酸的新方法，该方法使用用C-5 N-三氟乙酰基（NHTFA）取代基保护的亚磷酸酯唾液酸供体。与传统供体相比，这些供体在糖苷键形成过程中具有更高程度的α-异头选择性，并且在寡唾液酸合成的迭代唾液酸化过程中具有更高的产率。