Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

fn3123 scheme

Acta Cryst. (2013). C69, 282-284 [ doi:10.1107/S0108270113000395 ]

2,2'-Anhydro-1-(3',5'-di-O-acetyl--D-arabinofuranosyl)uracil, a cyclouridine nucleoside with a C4'-endo furanosyl conformation

Y. Fu, Y.-X. He, H.-X. Hou, W.-B. Zhu, H.-L. Li, C. Wu and F.-Y. Xian

Abstract: 2,2'-Anhydro-1-(3',5'-di-O-acetyl- [beta] -D-arabinofuranosyl)uracil, C₁₃H₁₄N₂O₇, was obtained by refluxing 2',3'-O-(methoxymethylene)uridine in acetic anhydride. The structure exhibits a nearly perfect C4'-endo (⁴E) conformation. The best four-atom plane of the five-membered furanose ring is O-C-C-C, involving the C atoms of the fused five-membered oxazolidine ring, and the torsion angle is only -0.4 (2)°. The oxazolidine ring is essentially coplanar with the six-membered uracil ring [r.m.s. deviation = 0.012 (5) Å and dihedral angle = -3.2 (3)°]. The conformation at the exocyclic C-C bond is gauche-trans which is stabilized by various C-H [pi] and C-O [pi] interactions.

Formula: C₁₃H₁₄N₂O₇


	Chemdraw file (11.3 kbytes) [ doi:10.1107/S0108270113000395/fn3123Isup3.cdx ] Supplementary material

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