Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation
Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation
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DOI：
10.1016/j.tetlet.2007.08.088
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发表时间：
2007-10-15
影响因子：
1.8
通讯作者：
Sato, Masayuki
中科院分区：
文献类型：
--
作者：
Ikeda, Kiyoshi;Miyamoto, Keisuke;Sato, Masayuki
月桂基硫代唾液酸糖苷的5-N-叔丁氧羰基（Boc）基团和环戊基甲基醚（CPME）作为溶剂的组合增强了唾液酸化期间唾液酸供体的反应性和α-选择性。Yb（OTf）（3）-SiO2成功地实现了唾液酸糖苷的N-Boc基团（包括酸敏感的异亚丙基官能团）的选择性脱保护。NN-Ac，Boc转化为唾液酸糖苷的N-乙酰基乙醇酰基容易地通过混合Ac-N-Boc氨基甲酸酯的选择性N-脱酰化、随后的Boc基团去除和酰化来进行。(C)2007爱思唯尔有限公司保留所有权利。
The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and alpha-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group of sialoside, including an acid-sensitive isopropylidene function, was successfully achieved by Yb(OTf)(3)-SiO2. Transformation of NN-Ac,Boc into an N-acetylglycolyl group of sialoglycoside was easily performed via selective N-deacylation of the mixed Ac-N-Boc carbamate, subsequent Boc group removal, and acylation. (C) 2007 Elsevier Ltd. All rights reserved.