Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation

被引:365
作者
Crich, D
Sun, SX
机构
[1] Department of Chemistry, University of Illinois at Chicago, Chicago, IL 60607-7061
关键词
D O I
10.1021/ja971239r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.
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页码:11217 / 11223
页数:7
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