SYNTHESIS OF 2-OXA-4-AZABICYCLO[3.2.1]OCTANE AND 2-OXA-4-AZABICYCLO[3.2.1]OCTENE SYSTEMS VIA X-RAY-ANALYZED TRANS-3-DIBENZAMIDO-CYCLOPENTENE-1-OXIDE

被引：7
作者：
LEGRAVEREND, M [1 ]
HUEL, C [1 ]
GUILHEM, J [1 ]
BISAGNI, E [1 ]
机构：
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
来源：
CARBOHYDRATE RESEARCH | 1992年 / 228卷 / 01期
关键词：
D O I：
10.1016/S0008-6215(00)90545-7
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
3,4-trans-Epoxidation of (cyclopent-3-en-1-yl)dibenzamide gave, in 82% yield, the 1,5-epoxide, the structure of which was confirmed by X-ray crystallographic analysis. Epoxide ring opening by trimethylsilyl cyanide, under the catalysis of diethylaluminum chloride, did not lead to the expected trans-beta-trimethylsilyl-oxynitrile as a potential precursor of carbocyclic 2-deoxy-D-erythro-pentofuranosylamine, but to 4-benzamido-3-cyano-3-phenyl-7-trimethylsilyloxy-2-oxa-4-azabicyclo[3.2.1]octane, which resulted from the participation of the benzoyl group in the epoxide ring cleavage.
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页码：21 / 27
页数：7
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