Synthesis of d - and l -apio nucleoside analogues with 2′-hydroxyl group as potential anti-HIV agents
| Autor: | Dong Zhe Jin, Hea Ok Kim, Prashantha Gunaga, Moon Woo Chun, Hyung Ryong Moon, Dae-Kee Kim, Sung Hee Kwon, Lak Shin Jeong |
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| Rok vydání: | 2004 |
| Předmět: |
Anti-HIV Agents
Chemistry Dideoxynucleosides Stereochemistry Organic Chemistry Clinical Biochemistry Enantioselective synthesis Galactose Pharmaceutical Science Stereoisomerism Biochemistry Chemical synthesis Dihydroxylation Cell Line Tumor Drug Discovery HIV-1 Humans Molecular Medicine Stereoselectivity Molecular Biology Deoxygenation Nucleoside |
| Zdroj: | Bioorganic & Medicinal Chemistry. 12:1101-1109 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2003.12.002 |
| Popis: | The present work describes the asymmetric synthesis of D- and L-apio-2',3'-dideoxynucleoside analogues, 4 and 5 with 2'-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure. |
| Databáze: | OpenAIRE |
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