On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides
On the stereoselectivity of glycosidation of thiocyanates, thioimidates, and thioglycosides
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DOI：
10.1016/j.carres.2010.08.003
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发表时间：
2010-10-13
影响因子：
3.1
通讯作者：
Demchenko, Alexei V.
中科院分区：
文献类型：
--
作者：
Kaeothip, Sophon;Akins, Steven J.;Demchenko, Alexei V.
比较并排糖基化研究表明，糖基硫氰酸酯，硫代亚氨酸，和硫代糖苷类提供比较立体选择性的糖基化。非常高的α-立体选择性，以前记录的糖基硫氰酸酯可以实现，但只有当糖基受体配备有吸电子酰基取代基。部分苄基化的糖基受体提供相对适度的立体选择性，这与其他常见的糖基供体相当。因此，硫代亚氨酸和硫代糖苷类显示出类似于硫氰酸酯的高立体选择性，具有不同类别的酰化伯和仲糖基受体。(C)2010爱思唯尔有限公司版权所有。
Comparative side-by-side glycosylation studies demonstrated that glycosyl thiocyanates, thioimidates, and thioglycosides provide comparative stereoselectivities in glycosylations. Very high alpha-stereoselectivity that was previously recorded for glycosyl thiocyanates can be achieved, but only if glycosyl acceptors are equipped with electron-withdrawing acyl substituents. Partially benzylated glycosyl acceptors provided relatively modest stereoselectivity, which was on a par with other common glycosyl donors. Accordingly, thioimidates and thioglycosides showed high stereoselectivity similarly to that of thiocyanates with different classes of acylated primary and secondary glycosyl acceptors. (C) 2010 Elsevier Ltd. All rights reserved.