Synthesis of 3′-N-Substituted 3′-Amino-3′-Deoxythymidine Derivatives
- 1 November 1993
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 12 (9) , 951-966
- https://doi.org/10.1080/07328319308018565
Abstract
A series of 3′-N-substituted 3′-amino-3′-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-0-mesyl-5-0-trityl-β-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3′-amino-5′-0-trityl-3′-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3′-amino-3′-deoxythymidine from 3′ -azido-5′-0-trityl-3′-deoxythymidine using sodium borohydride was also described.Keywords
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