A STRAIGHTFORWARD SYNTHESIS OF (+ -) 5-AMINO-5,6-DIDEOXYALLOSE, OF ITS BISULFITE BETA-ANOMER, AND OF ITS 1-DEOXY DERIVATIVE/

Authors
DEFOIN A SARAZIN H STREITH J
Citation
A. Defoin et al., A STRAIGHTFORWARD SYNTHESIS OF (+ -) 5-AMINO-5,6-DIDEOXYALLOSE, OF ITS BISULFITE BETA-ANOMER, AND OF ITS 1-DEOXY DERIVATIVE/, Tetrahedron letters, 34(27), 1993, pp. 4327-4330
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
27
Year of publication
1993
Pages
4327 - 4330
Database
ISI
SICI code
0040-4039(1993)34:27<4327:ASSO(->2.0.ZU;2-P
Abstract
Diels-Alder cycloaddition of (E,E)-hexadienal dimethylacetal 3 with th e benzyloxycarbonylnitroso dienophile 4, followed by catalytic osmylat ion, hydrogenolysis, and treatment with SO2, led stereospecifically to the sole beta-anomer of allopiperidinose bisulfite derivative 7. Sapo nification of 7 and thence catalytic hydrogenation gave in high yield the 1-deoxyallopiperidine derivative 9.