Add time:08/07/2019         Source:sciencedirect.com

1-(2-Azido-2,3,-dideoxy-β-D-erythro-pentofuranosyl)thymine (2′-N3ddThd) was synthesized from 1-(5-O-trithyl-2,3-anhydro-β-D-lyxofuranosyl)thymine by two different procedures. Method A prepared the title compound by opening of the oxirane ring with LiEt3BH followed by mesylation of the 2′-hydroxyl function, introduction of the 2′-azido substituent and deblocking of the 5′-function. In method B nucleophilic opening of 3′-deoxy-5′-O-(tert-butyldimethylsilyl)-5-methyl-2,2′-anhydrouridine was carried out with sodium azide in hexamethylphos-phoramide in the presence of benzoic acid. Single X-ray crystallographic studies indicated a solid state conformation (3T2), which was opposite to that of the A form of AZT (2T3) but closely resembled that of 1-(2-fluoro-2,3-dideoxy-β-D-erythropentofuranosyl)thymine (2′-FddThd) (3T2) and of 3′-azido-2′,3′-dideoxy-2,6-diaminopurine riboside (3′-N3ddDAP) (3T2). Whereas the latter displayed significant inhibitory activity against human immunodeficiency virus (HIV) replication, 2′-FddThd and 2′-N3ddThd were essentially inactive.

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