Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors
Armed-disarmed effect of remote protecting groups on the glycosylation reaction of 2,3-dideoxyglycosyl donors
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DOI：
10.1016/j.tetlet.2011.02.109
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发表时间：
2011-05-04
影响因子：
1.8
通讯作者：
Toshima, Kazunobu
中科院分区：
文献类型：
--
作者：
Tomono, Satoshi;Kusumi, Shunichi;Toshima, Kazunobu
研究了C-4和/或C-6位上的远程保护基团对2，3-双脱氧糖基供体的糖基化反应的解除武装效应。发现在各种糖基化条件下，4-或6-O-Bn 2，3-二脱氧糖基供体比相应的4，6-di-O-Bz 2，3-二脱氧糖基供体反应性更高。基于这些结果，实现了使用4，6-二-O-Bn糖基乙酸酯和4-OH-6-O-Bz糖基乙酸酯的有效的和化学选择性的糖基化反应，以良好的产率和高α-立体选择性生产2，3-二脱氧二糖。(C)2011爱思唯尔有限公司保留所有权利。
The armed disarmed effect of remote protecting groups at the C-4 and/or C-6 position(s) on the glycosylation reactions of 2,3-dideoxyglycosyl donors was investigated. It was found that under various glycosylation conditions, 4- or 6-O-Bn 2,3-dideoxyglycosyl donors were much more reactive than the corresponding 4,6-di-O-Bz 2,3-dideoxyglycosyl donors. Based on these results, an effective and chemoselective glycosylation reaction using 4,6-di-O-Bn glycosyl acetate and 4-OH-6-O-Bz glycosyl acetate was realized, producing a 2,3-dideoxydisaccharide in good yield with high alpha-stereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.