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使用硝酸铈(IV)铵、碘化钠和乙酸对糖烯进行碘乙酰氧基化反应:2-脱氧-2-碘-α-甘露吡喃糖基乙酸酯的立体选择性合成

Iodoacetoxylation of glycals using cerium(IV) ammonium nitrate, sodium iodide, and acetic acid: stereoselective synthesis of 2-deoxy-2-iodo-alpha-mannopyranosyl acetates.

作者信息

Roush W R, Narayan S, Bennett C E, Briner K

机构信息

Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.

出版信息

Org Lett. 1999 Sep 23;1(6):895-7. doi: 10.1021/ol990815g.

DOI:10.1021/ol990815g
PMID:10823219
Abstract

[formula: see text] The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-alpha-mannopyranosyl acetates with good stereoselectivity. In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iodosuccinimide and HOAc.

摘要

[化学式:见正文] 在乙酸存在下,糖醇与硝酸铈(IV)铵和碘化钠的反应以良好的立体选择性提供2-脱氧-2-碘-α-甘露吡喃糖基乙酸酯。在所研究的大多数情况下,该选择性比使用N-碘代琥珀酰亚胺和乙酸的反应的选择性要好得多。

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