| Autor: |
M J, Robins, B, Doboszewski, V A, Timoshchuk, M A, Peterson |
| Rok vydání: |
2000 |
| Předmět: |
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| Zdroj: |
The Journal of organic chemistry. 65(10) |
| ISSN: |
0022-3263 |
| Popis: |
Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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