Synthesis, molecular structure and physicochemical properties of bis(3 `-azido-3 `-deoxythymidin-5 `-yl) carbonate

3`-Azido-3`-deoxythymidine (zidovudine, AZT), a synthetic analog of natural nucleoside thymidine, has been used extensively in AIDS treatments. We report here the synthesis. X-ray crystal and molecular structure, NMR, IR and Raman spectra and the thermal behavior of a novel carbonate of AZT [(AZT-O)(2)C=O], prepared by the reaction of zidovudine with carbonyldiimidazole. The carbonate compound, C(21)H(24)N(10)O(9), crystallizes in the tetragonal space group P4(1)2(1)2 with a = b = 15.284(1), c = 21.695(1) angstrom, and Z = 8 molecules per unit cell. It consists of two AZT moieties of closely related conformations which are bridged by a carbonyl group to adopt a folded Z-like shape. (C) 2010 Elsevier B.V. All rights reserved.Fondo para la Investigacion Cientifica y Tecnologica (FONCyT)Fondo para la Investigacion Cientifica y Tecnologica (FONCyT)Secretaria de Ciencia y Tecnica de la Universidad Nacional de Cordoba (SECyT-UNC)Secretaria de Ciencia y Tecnica de la Universidad Nacional de Cordoba (SECyT-UNC)FAPESP of BrazilFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Consejo Nacional de Investigaciones Cientificas y Tecnologicas (CONICET)[PIP 1125]Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina (CONICET)Comision de Investigaciones Cientificas de la Provincia de Buenos Aires (CICPBA), ArgentinaComisión de Investigaciones Científicas Provincia de Buenos Aires (CIC) - ArgentinaUNLPUNLPANPCyT of Argentina[PICT 10968]Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT