SOLUTION-PHASE SYNTHESIS OF DITHYMIDINE PHOSPHOROTHIOATE BY A PHOSPHOTRIESTER METHOD USING NEW S-PROTECTING GROUPS

Authors
PUSCHL A KEHLER J DAHL O
Citation
A. Puschl et al., SOLUTION-PHASE SYNTHESIS OF DITHYMIDINE PHOSPHOROTHIOATE BY A PHOSPHOTRIESTER METHOD USING NEW S-PROTECTING GROUPS, Nucleosides & nucleotides, 16(1-2), 1997, pp. 145-158
Citations number
29
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
16
Issue
1-2
Year of publication
1997
Pages
145 - 158
Database
ISI
SICI code
0732-8311(1997)16:1-2<145:SSODPB>2.0.ZU;2-J
Abstract
A phosphotriester method for the synthesis of dithymidine phosphorothi oates with eight S-protecting groups has been investigated. Three of t he S-protecting groups possesed catalytic activity, however side react ions occurred under deprotection. The best S-protecting group was 4-ch loro-2-nitrobenzyl which could be removed with a minimum of side react ions (0.3%). The Coupling reagent PyFNOP (11) gave protected dithymidi ne phosphorothioate in 96% yield after 15 min coupling.