A simple multi-gram synthesis of 5’-hydrogenphosphonates and s’-phosphorofluoridates of sugar modified nucleosides1 Journal Article
| Authors: | Matulic-Adamic, J.; Rosenberg, I.; Arzumanov, A. A.; Dyatkina, N. B.; Shirokova, E. A.; Krayevsky, A. A.; Watanabe, K. A. |
| Article Title: | A simple multi-gram synthesis of 5’-hydrogenphosphonates and s’-phosphorofluoridates of sugar modified nucleosides1 |
| Abstract: | Treatment of 3’-fluoro-3'-deoxythymidine (FLT), 3’-azido-3,-deoxythymidine (AZT) and 2’, 3’-dideoxyadenosine (ddA) with tris(l, l, l, 3, 3, 3-hexafluoro-2-propyl)phosphite or phosphorous acid and N, N’-dicyclohexylcarbodiimide produced the corresponding nucleoside S’-hydrogenphosphonates. Reaction of FLT, AZT and 3’-deoxythymidine (ddT) with fluorophosphoric acid and 2, 4, 6-triisopropylbenzenesulfonyl chloride lead to the corresponding nucleoside 5’-phosphorofluoridates also on a multi-gram scale. All the compounds were isolated in high pure state by chromatographic technique. © 1993, Taylor & Francis Group, LLC. All rights reserved. |
| Keywords: | controlled study; nonhuman; human immunodeficiency virus infection; mouse; animal experiment; chemical structure; human immunodeficiency virus; high performance liquid chromatography; sodium; nuclear magnetic resonance; chemical reaction; synthesis; antiviral activity; zidovudine; phosphonic acid derivative; 3' fluorothymidine; intraperitoneal drug administration; nucleotide metabolism; nucleoside derivative; article; fluorine derivative; 2',3' dideoxyadenosine; dicyclohexylcarbodiimide; phosphoric acid derivative; phosphorous acid |
| Journal Title: | Nucleosides & Nucleotides |
| Volume: | 12 |
| Issue: | 10 |
| ISSN: | 0732-8311 |
| Publisher: | Taylor & Francis Inc. |
| Date Published: | 1993-12-01 |
| Start Page: | 1085 |
| End Page: | 1092 |
| Language: | English |
| DOI: | 10.1080/07328319308016206 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 1 March 2019 -- Source: Scopus |
