A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS

Authors
LAY L NICOTRA F PAGANINI A PANGRAZIO C PANZA L
Citation
L. Lay et al., A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS, Tetrahedron letters, 34(28), 1993, pp. 4555-4558
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
28
Year of publication
1993
Pages
4555 - 4558
Database
ISI
SICI code
0040-4039(1993)34:28<4555:ANPFTS>2.0.ZU;2-F
Abstract
Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the amin oalcohol 3. 3 is an useful precursor of azasugars: it is converted int o the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation wi th PCC it affords the lactam 5 which can be reduced to the correspondi ng amine 6.