Journal of the Chemical Society. Perkin transactions I p. 2573 - 2576 (1985)
Update date:2022-08-04
Topics:
Seela, Frank
Steker, Herbert
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 percent.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.
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Doi:10.1021/jo01369a017
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