2-位氧化糖羰基转位反应的研究  

A Novel Carbonyl Transposition Reaction Led by Aromatic Amine's Nucleophilic Addition to 2-Oxo Glycoside

作　　者：刘宏民[1] 徐汶[1] 刘振中[1] 

机构地区：[1]郑州大学化学化工学院,郑州450052

出　　处：《高等学校化学学报》2001年第10期1682-1684,共3页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金 (批准号 :2 96 772 0 30 )资助

摘　　要：A novel carbonyl transposition reaction led by aromatic amines nucleophilic addition to \{2 oxo glycoside\} was discovered. The mechanism of the reaction was provided through tracing the change of 1H NMR of a hemiacetal intermediate which was obtained in the reaction of o phenylene diamine with 2 oxo glycoside. Both the intermediate and the product were identified by FTIR, 1H NMR, 13 C NMR, 1H 1H COSY and 1H 13 C COSY spectra. The other aromatic amines reaction with 2 oxo glycoside also proved the mechanism. This reaction provides a new method for preparing 2 deoxy 2 aromatic amino 3 oxo glycosides, which is a new kind of material used in assymetric synthesis.A novel carbonyl transposition reaction led by aromatic amines nucleophilic addition to \{2 oxo glycoside\} was discovered. The mechanism of the reaction was provided through tracing the change of 1H NMR of a hemiacetal intermediate which was obtained in the reaction of o phenylene diamine with 2 oxo glycoside. Both the intermediate and the product were identified by FTIR, 1H NMR, 13 C NMR, 1H 1H COSY and 1H 13 C COSY spectra. The other aromatic amines reaction with 2 oxo glycoside also proved the mechanism. This reaction provides a new method for preparing 2 deoxy 2 aromatic amino 3 oxo glycosides, which is a new kind of material used in assymetric synthesis.

关 键 词：2-位氧化糖 羰基转位反应 芳胺 氨基糖 不对称合成 α-甲基-D-葡萄糖苷 2-位羰基衍生物 

分 类 号：O629.13[理学—有机化学] Q53[理学—化学]