Azines and azoles: CXXVII. Glycosylation of 5,7-dihydro-4H-pyrano-[2,3-d:6,5-d′]dipyrimidine-4,6(3H)-dione and its 5-phenyl-substituted analog
| Autor: | A. V. Moskvin, E. P. Studentsov, V. V. Kvasha, B. A. Ivin, E. V. Fedorova |
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| Rok vydání: | 2007 |
| Předmět: | |
| Zdroj: | Russian Journal of General Chemistry. 77:589-595 |
| ISSN: | 1608-3350 1070-3632 |
| Popis: | Glycosylation of 5-phenylpyrano[2,3-d:6,5-d′]dipyrimidine-4,6-diones through the corresponding di-O-trimethylsilyl derivative with excess 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose gives a mixture of 3-mono-and 3,7-bis(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-phenylpyrano[2,3-d:6,5-d′]dipyrimidines; in the reaction with equimolar amounts of the reactants, only the monoriboside is formed. Isomeric N,N′-disubstituted pyranodipyrimidines, as well as mixtures of their mono-and disubstituted derivatives can be separated by fractional crystallization. The alkylation of pyrano[2,3-d:6,5-d′]dipyrimidine-4,6-dione and its 5-phenyl-substituted derivative with 2-oxabutane-1,4-diyl diacetate provides an efficient procedure for the synthesis of acyclic analogs of glycosides based on pyrano[2,3-d:6,5-d′]dipyrimidines. |
| Databáze: | OpenAIRE |
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