6-Aza-2'-deoxyuridine and N(3)-anisoyl-6-aza-2'-deoxyuridine
Frank Seela1, Padmaja Chittepu, Yang He
1Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Abstract:
In 2-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione (6-aza-2'-deoxyuridine), C(8)H(11)N(3)O(5), (I), the conformation of the glycosylic bond is between anti and high-anti [chi = -94.0 (3) degrees ], whereas the derivative 2-(2-deoxy-beta-D-erythro-pentofuranosyl)-N(4)-(2-methoxybenzoyl)-1,2,4-triazine-3,5(2H,4H)-dione (N(3)-anisoyl-6-aza-2'-deoxyuridine), C(16)H(17)N(3)O(7), (II), displays a high-anti conformation [chi = -86.4 (3) degrees]. The furanosyl moiety in (I) adopts the S-type sugar pucker ((2)T(3)), with P = 188.1 (2) degrees and tau(m) = 40.3 (2) degrees, while the sugar pucker in (II) is N ((3)T(4)), with P = 36.1 (3) degrees and tau(m) = 33.5 (2) degrees. The crystal structures of (I) and (II) are stabilized by intermolecular N-H...O and O-H...O interactions.
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