Pyrrolidine analogues of 2′,3′-dideoxynucleosides: synthesis via 9-aminopurines and 1-aminopyrimidines
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2073-2079
- https://doi.org/10.1039/p19910002073
Abstract
Analogues of 2′,3′-dideoxynucleosides in which the tetrahydrofuran ring is replaced by a pyrrolidine ring linked to the base through an N–N bond have been prepared. The adenine 26, guanine 25 and hypoxanthine 27 compounds were synthesised via 9-aminopurines. Corresponding derivatives of 5-iodouracil 31, 5-chlorouracil 33 and 5-chlorocytosine 35 were prepared by substitution at the 5-position of hydroxy protected uracil derivatives. Enantiomers, 40a and 40b, of the pyrrolidine analogue of dideoxycytidine were prepared from 1-aminocytosine. The novel N-aminobases 9-aminoadenine 10, 1-aminocytosine 13 and 1-aminothymine 15 are described.Keywords
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