STEREOSELECTIVE REACTIONS OF RO-2,3-DIDEOXY-3-NITRO-BETA-D-HEXOPYRANOSYL)URACIL WITH SOME NUCLEOPHILES

Authors
OHTA N MINAMOTO K YAMAMOTO T KOIDE N SAKODA R
Citation
N. Ohta et al., STEREOSELECTIVE REACTIONS OF RO-2,3-DIDEOXY-3-NITRO-BETA-D-HEXOPYRANOSYL)URACIL WITH SOME NUCLEOPHILES, Nucleosides & nucleotides, 15(4), 1996, pp. 833-855
Citations number
29
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
15
Issue
4
Year of publication
1996
Pages
833 - 855
Database
ISI
SICI code
0732-8311(1996)15:4<833:SROR>2.0.ZU;2-#
Abstract
Michael addition of benzylamine, piperidine, morpholine, pyrrolidine, cyclohexylamine, allylamine and dimethylmalonate to the nitroolefin (5 ) generated in situ from idene-3-deoxy-3-nitro-beta-D-glucopyranosyl)u racil (4b) gave the corresponding ted-amino)-3-deoxy-3-nitro-beta-D-gl ucopyranosides (6a-f and 6h). Reaction of 4b with N,N'-carbonyldiimida zole directly gave 6g. Compound 4b was converted into the 2-deoxy anal ogue (8), which was reduced to the 3-amino (9) and 3-hydroxylamino ana logue (10).