Skip Navigation

This Article
Right arrow Print PDF (867K)
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrow Commercial Re-use Guidelines
for Open Access NAR Content
Google Scholar
Right arrow Articles by Halmos, T.
Right arrow Articles by Antonakis, K.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Halmos, T.
Right arrow Articles by Antonakis, K.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

Nucleic Acids Research, 1989, Vol. 17, No. 19 7663-7670
© 1989

CHEMISTRY

The synthesis of branched-chain 3'-C-cyanomethyl-2',3'-dideoxy sugar nucleosides of adenine as potential inhibitors of the human immunodeficiency virus

Thérèse Halmos, Roland Montserret and Kostas Antonakis

Institut de Recherches Scientifiques sur le Cancer du CNRS 94802 Villejuif Cedex, France

Received July 11, 1989. Revised August 31, 1989. Accepted August 31, 1989.

Condensation of the 3'-ketonucleoside 4 with diethyl cyanomethylphosphonate by a Wittig reaction afforded, after reduction of the unsaturated branched chain sugar nucleoside 5 with sodium borohydride, a mixture of 9-(2',5'-di-O-t-butyldimethylsilyl-3'-C-cyanomethyl-3'-deoxy-ß-D-ribo- and xylofuranosyl) adenines 6 and 7, which were separated after selective removal of the 5'-O-tBDMS group. Acetylation gave the monoacetylated ribo- and the triacetylated xylo compounds 10 and 11. Desilylation using tetrabutylammonium fluoride afforded the partially protected ribo isomer 12. The same treatment of 11 was accompanied by a N-O transacetylation giving the fully protected xylo compound 13a, from which the 2'-O-acetyl group was selectively removed using hydroxylaminium acetate. Treatment of 12 and 13b with phenoxythiocarbonyl chloride followed by deoxygenation with tributyltin hydride in the presence of azobisisobutyronitrile, and deacetylation in methanol saturated with ammonia afforded 9-(3'-C-cyanomethyl-2',3'-dideoxy-ß-D-erythro-pentofuranosyl) adenine 2 and 9-(3'-C-cyanomethyl-2'3'-dideoxy-ß-D-threo-pentofuranosyl) adenine 3.


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?




Disclaimer:
Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.