Synthesis and hydrolytic stability of 4-substituted pyrazolo[3,4-d]pyrimidine 2′-deoxyribofuranosides
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2573-2576
- https://doi.org/10.1039/p19850002573
Abstract
Phase-transfer glycosylation of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (2) yielded the N-1 glycosylation product (3) in 42%. The protected intermediate (3) was converted into pyrazolo[3,4-d]pyrimidine 2′-deoxyribofuranosides with amino, oxo, and thioxo substituents at C-4. Kinetic data of proton-catalysed hydrolysis showed that pyrazolo[3,4-d]pyrimidine 2′-deoxyribofuranosides are more stable at the N-glycosylic bond than are the parent purine nucleosides.This publication has 2 references indexed in Scilit:
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