EPIMERIZATION AT C2 OF METHYL O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-PENTOFURANOSIDES UPON OXIDATION

Authors
MIKHAILOPULO IA SIVETS GG POOPEIKO NE KHRIPACH NB
Citation
Ia. Mikhailopulo et al., EPIMERIZATION AT C2 OF METHYL O-BENZYL-2-DEOXY-2-FLUORO-ALPHA-D-PENTOFURANOSIDES UPON OXIDATION, Nucleosides & nucleotides, 14(3-5), 1995, pp. 381-382
Citations number
5
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
14
Issue
3-5
Year of publication
1995
Pages
381 - 382
Database
ISI
SICI code
0732-8311(1995)14:3-5<381:EACOMO>2.0.ZU;2-N
Abstract
Oxidation of 1 with DMSO-acetic anhydride resulted in the formation of a mixture of epimeric ketones 2 and 3 in the ratio of approximate to 3:1 in high combined yield. Acetolysis of methyl glycoside 5 afforded i-O-benzoyl-2-deoxy-2-fluoro-beta-D-ribofuranoside (6)(83%). The latte r was reacted with silylated N-6-benzoyladenine to give alpha- and bet a-ribosides (1:3.7; 61%, combined).