| Autor: |
Varizhuk AM; Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia., Kochetkova SV, Kolganova NA, Timofeev EN, Florent'ev VL |
| Jazyk: |
ruština |
| Zdroj: |
Bioorganicheskaia khimiia [Bioorg Khim] 2009 Sep-Oct; Vol. 35 (5), pp. 650-6. |
| DOI: |
10.1134/s1068162009050082 |
| Abstrakt: |
A method for the synthesis of 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides has been developed. 3-O-Benzyloxymethyl-1,2-O-isopropylidene-alpha-D-allofuranose was oxidized by sodium periodate to form a 5-aldo derivative, which was converted by the reaction with triethylphosphonoacetate in the presence of sodium hydride into a 5-deoxy-5-ethoxycarbonylmethylene derivative. The hydration of the unsaturated compound gave 5-deoxy-5-ethoxycarbonylmethyl-l,2-O-isopropylidene-alpha-D-ribofuranose. After the benzylation of 3-hydroxyl, the removal of the isopropylidene group by heating with acetic acid, and the subsequent acetylation, l,2-di-O-acetyl-3-O-benzyl-5-deoxy-5-ethoxycarbonylmethyl-D-ribofuranose was obtained, which reacted with persilylated nucleic acid bases to form 5'-deoxy-5'-ethoxycarbonylmethyl nucleosides. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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