Epimerization at C2 of methyl 5-O-benzyl-2-deoxy-2-fluoro-α-D- pentofuranosides upon oxidation

Article abstract of DOI:10.1080/15257779508012388

Oxidation of 1 with DMSO-acetic anhydride resulted in the formation of a mixture of epimeric ketones 2 and 3 in the ratio of ?3:1 in high combined yield. Acetolysis of methyl glycoside 5 afforded 1-O-acetyl-3,5-di-O- benzoyl-2-deoxy-2-fluoro-β-D-ribofuranoside (6)(83%). The latter was reacted with silylated N⁶-benzoyladenine to give α- and β-ribosides (1:3.7; 61%, combined).

Full text of DOI:10.1080/15257779508012388

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Epimerization at C2 of Methyl 5-
O-Benzyl-2-deoxy-2-fluoro-α-D-
pentofuranosides upon Oxidation
Igor A. Mikhailopulo a , Grigorii G. Sivets a , Nicolai E. Poopeiko a
Natalia B. Khripach a
&
a Institute of Bioorganic Chemistry, Byelorussian Academy of
Sciences , 220141, Minsk, Zhodinskaya, 5/2, Byelorussia
Published online: 16 Feb 2007.
To cite this article: Igor A. Mikhailopulo , Grigorii G. Sivets , Nicolai E. Poopeiko & Natalia B. Khripach
(1995) Epimerization at C2 of Methyl 5-O-Benzyl-2-deoxy-2-fluoro-α-D-pentofuranosides upon
Oxidation, Nucleosides and Nucleotides, 14:3-5, 381-382
To link to this article: http://dx.doi.org/10.1080/15257779508012388
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