SYNTHESIS OF AZASUGARS .1. ISOMERIZATION OF POLYHYDROXYLATED PIPERIDINES

Authors
POITOUT L LEMERRER Y DEPEZAY JC
Citation
L. Poitout et al., SYNTHESIS OF AZASUGARS .1. ISOMERIZATION OF POLYHYDROXYLATED PIPERIDINES, Tetrahedron letters, 37(10), 1996, pp. 1609-1612
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
10
Year of publication
1996
Pages
1609 - 1612
Database
ISI
SICI code
0040-4039(1996)37:10<1609:SOA.IO>2.0.ZU;2-1
Abstract
l-3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol and L-gulitol under go easy isomerization, mainly either by ring contraction, or either by SN2 inv,ersion at C2. This isomerization performed by bis-hydroxyl ac tivation allows to access to 2,5-dideoxy-2,5-imino-L-iditol, 5-epi-DNJ , DMDP, and DMJ.