Tanaka Hiroshi, Nishiura Yuji, Takahashi Takashi
Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1-S1-35, Oookayama, Meguro, Tokyo 152-8552, Japan.
J Am Chem Soc. 2006 Jun 7;128(22):7124-5. doi: 10.1021/ja0613613.
An efficient and elegant synthesis of alpha(2,8)-oligosialosides is described. The 5-N,4-O-carbonyl-protected sialyl donor undergoes alpha-sialylation in CH2Cl2 to give alpha(2,8)- and alpha(2,9)-disialosides in excellent yields. The 5-N,4-O-carbonyl protecting group was effective in improving the reactivity of the C8 hydroxyl groups toward glycosylation. Using the sialyl building block, the synthesis of tetra-alpha(2,8)-sialic acid was accomplished by using a simple glycosidation and deprotection protocol.
本文描述了一种高效且简洁的α(2,8)-寡唾液酸苷的合成方法。5-N,4-O-羰基保护的唾液酸供体在二氯甲烷中进行α-唾液酸化反应，以优异的产率得到α(2,8)-和α(2,9)-二唾液酸苷。5-N,4-O-羰基保护基有效地提高了C8羟基对糖基化反应的反应活性。使用该唾液酸构建模块，通过简单的糖基化和脱保护方案完成了四-α(2,8)-唾液酸的合成。
