FACILE SYNTHESIS OF 3'-C-BRANCHED 1,5-ANHYDROHEXITOL NUCLEOSIDES

Authors
HOSSAIN N HERDEWIJN P
Citation
N. Hossain et P. Herdewijn, FACILE SYNTHESIS OF 3'-C-BRANCHED 1,5-ANHYDROHEXITOL NUCLEOSIDES, Nucleosides & nucleotides, 17(9-11), 1998, pp. 1781-1786
Citations number
12
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
17
Issue
9-11
Year of publication
1998
Pages
1781 - 1786
Database
ISI
SICI code
0732-8311(1998)17:9-11<1781:FSO31N>2.0.ZU;2-H
Abstract
The 3'-beta-C-branched anhydrohexitol nucleosides have been convenient ly synthesised starting from commercially available D-ribose following the reaction sequence: (i) conversion of protected pentofuranose suga r to the corresponding hexopyranosyl nitrosugar (ii) addition of the c onjugate base of nitrosugar to formaldehyde to obtain C-branched nitro sugar (iii) removal of nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to build up the nucleobase.