Synthesis of phosphoceramide azidothymidine and phosphoceramide didehydrodeoxythymidine
Oskolkova, O.V.; Perepelov, A.V.; Esipov, D.S.; Zamiatina, A.I.; Alekseeva, S.G.; Shvets, V.I.
Bioorganicheskaia Khimiia 23(7): 591-596
1997
ISSN/ISBN: 0132-3423 PMID: 9471979 Document Number: 476843
The synthesis of two novel lipophosphonucleoside potential antiviral agents, 2-stearoyl-rac-sphinganine-1-phosphoryl-5'-(3'-deoxy-3'-azido)thymidine and 2-stearoyl-rac-sphinganine-1-phosphoryl-5'-(2',3'-didehydro-2', 3'-dideoxy)thymidine, is reported. The phosphoester linkages between the primary hydroxyl group of rac-ceramide and the 5'-hydroxyl group of the corresponding 3'-deoxythymidine derivative were formed using either the H-phosphonate or the phosphite triester method. The H-phosphonate approach was shown to be the method of choice for the synthesis of ceramide phospho-3'-azidothymidine.