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