使用5-N,7-O-羰基保护的唾液酸供体的唾液酸化反应：腈溶剂辅助下的异常立体选择性。
Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistance.
作者信息
Tanaka Hidenori, Ando Hiromune, Ishihara Hideharu, Koketsu Mamoru
机构信息
Department of Chemistry, Faculty of Engineering, Gifu University, Gifu, Japan.
出版信息
Carbohydr Res. 2008 Jul 21;343(10-11):1585-93. doi: 10.1016/j.carres.2008.05.005. Epub 2008 May 8.
A 5-N,7-O-carbonyl-protected sialyl donor was synthesized, and, unexpectedly, this donor showed beta-selectivity (alpha/beta = 1/2.4-1/20) on coupling with sugar acceptors in acetonitrile upon treatment with various promoter systems. For the coupling reaction in dichloromethane, a modified Ellervik's method (IBr and AgClO(4).H(2)O) was highly effective in activating the 5-N,7-O-carbonyl donor, providing moderate alpha-selectivity (alpha/beta = ~1.8/1).
合成了一种5-N,7-O-羰基保护的唾液酸供体，出乎意料的是，在用各种促进剂体系处理后，该供体在乙腈中与糖受体偶联时表现出β选择性（α/β = 1/2.4 - 1/20）。对于在二氯甲烷中的偶联反应，改良的埃勒维克方法（IBr和AgClO₄·H₂O）在活化5-N,7-O-羰基供体方面非常有效，提供了适度的α选择性（α/β = ~1.8/1）。
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