HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (2'S)-[2'-H-2]-2'-DEOXYRIBONUCLEOSIDES FROM THE CORRESPONDING RIBONUCLEOSIDES

Authors
KAWASHIMA E AOYAMA Y RADWAN MF MIYAHARA M SEKINE T KAINOSHO M KYOGOKU Y ISHIDO Y
Citation
E. Kawashima et al., HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (2'S)-[2'-H-2]-2'-DEOXYRIBONUCLEOSIDES FROM THE CORRESPONDING RIBONUCLEOSIDES, Nucleosides & nucleotides, 14(3-5), 1995, pp. 333-336
Citations number
16
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
14
Issue
3-5
Year of publication
1995
Pages
333 - 336
Database
ISI
SICI code
0732-8311(1995)14:3-5<333:HDSO(>2.0.ZU;2-B
Abstract
The four (2'S)-[2'-H-2]-2'-deoxynucleosides (>90 atom % H-2),,ere synt hesized from the corresponding ribonucleosides involving six steps of reactions, i.e., oxidation of their 2'-hydroxyl group, stereoselective reductive deuteration of the resulting 2'-ketonucleoside intermediate s with (NaBH4)-H-2 in EtOH-H2O or EtOH, triflation, bromination with L iBr, highly stereoselective Bu(3)SnH-Et(3)B reduction of the resulting bromide, and, finally, unmasking.