2-Deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides.
2-Deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides.
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DOI：
10.1021/ol9908070
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发表时间：
1999-08
期刊：
影响因子：
5.2
通讯作者：
W. Roush;B. Gung;C. Bennett
中科院分区：
文献类型：
--
作者：
W. Roush;B. Gung;C. Bennett
[公式：见原文]2-脱氧-2-碘-和2-脱氧-2-溴代葡萄糖酰三氯乙酸酯8-10和22是2-脱氧- β -糖苷的非常有用的前体。这些活性糖基供体以TBS-OTf作为活化剂，与一系列糖基受体在-78℃下进行高度立体选择性的糖基化反应。在本文报道的七个例子中，有六个的β -糖苷的选择性为>或= 19:1。
[formula: see text] 2-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2-deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl acceptors using TBS-OTf as the activating agent. beta-Glycosides are obtained with > or = 19:1 selectivity in six of the seven examples reported herein.