Stereoselective synthesis of oligo-α-(2,8)-sialic acids
Stereoselective synthesis of oligo-α-(2,8)-sialic acids
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DOI：
10.1021/ja0613613
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发表时间：
2006-06-07
影响因子：
15
通讯作者：
Takahashi, Takashi
中科院分区：
文献类型：
--
作者：
Tanaka, Hiroshi;Nishiura, Yuji;Takahashi, Takashi
本文报道了α（2，8）-寡唾液酸糖苷的一种高效、简便的合成方法。5-N，4-O-羰基保护的唾液酸供体在CH 2Cl 2中进行α-唾液酸化，以优异的产率得到α（2，8）-和α（2，9）-双唾液酸糖苷。5-N，4-O-羰基保护基有效地改善了C8羟基对糖基化的反应性。以唾液酸为结构单元，通过简单的糖苷化和脱保护反应合成了四-α（2，8）-唾液酸。
An efficient and elegant synthesis of α(2,8)-oligosialosides is described. The 5-N,4-O-carbonyl-protected sialyl donor undergoes α-sialylation in CH2Cl2to give α(2,8)- and α(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-α(2,8)-sialic acid was accomplished by using a simple glycosidation and deprotection protocol.