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

Citation
T. Tschamber et al., STEREOSELECTIVE CATALYTIC DOUBLE OSMYLATION OF 1,2-DIHYDROPYRIDINES LEADING TO AMINO-ARABINOSE AND TO AMINO-ALTROSE DERIVATIVES AND TO POTENTIAL GLYCOSIDASE INHIBITORS, Tetrahedron, 50(4), 1994, pp. 1135-1152
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
50
Issue
4
Year of publication
1994
Pages
1135 - 1152
Database
ISI
SICI code
0040-4020(1994)50:4<1135:SCDOO1>2.0.ZU;2-D
Abstract
Catalytic double osmylation of 1,2-dihydropyridines 1b and 1c proceede d stereospecifically and in good yields to the corresponding aminoarab inose 2b, and aminoaltrose 2c derivatives, respectively. In basic medi um these piperidinoses equilibrated with their furanose isomers 6b and 6c (both alpha- and beta-anomers). Hydrogenolysis of their urethane m oieties led to the corresponding piperidine triols 7a and 7b.