STEREOSELECTIVE CATALYTIC DOUBLE OSMYLATION OF 1,2-DIHYDROPYRIDINES LEADING TO AMINO-ARABINOSE AND TO AMINO-ALTROSE DERIVATIVES AND TO POTENTIAL GLYCOSIDASE INHIBITORS

被引:29
作者
TSCHAMBER, T
BACKENSTRASS, F
NEUBURGER, M
ZEHNDER, M
STREITH, J
机构
[1] UNIV HAUTE ALSACE,ECOLE NATL SUPER CHIM,CNRS,SYNTH ORGAN CHIM MICROBIENNE LAB,F-68093 MULHOUSE,FRANCE
[2] UNIV BASEL,INST ANORGAN CHEM,CH-4056 BASEL,SWITZERLAND
关键词
D O I
10.1016/S0040-4020(01)80825-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic double osmylation of 1,2-dihydropyridines 1b and 1c proceeded stereospecifically and in good yields to the corresponding aminoarabinose 2b, and aminoaltrose 2c derivatives, respectively. In basic medium these piperidinoses equilibrated with their furanose isomers 6b and 6c (both alpha- and beta-anomers). Hydrogenolysis of their urethane moieties led to the corresponding piperidine triols 7a and 7b.
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页码:1135 / 1152
页数:18
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