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6-Amino-3-(β-d-2-de­oxy-erythro-furanos­yl)-2-fluoro­pyridine: a nucleoside analogue

✍ Scribed by Sun, Zhenhua ;Lo, Wayne ;McLaughlin, Larry W.

Book ID
104486800
Publisher
International Union of Crystallography
Year
2006
Tongue
English
Weight
302 KB
Volume
62
Category
Article
ISSN
1600-5368

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✦ Synopsis

The title compound [systematic name: (2__R__,3__R__,5__R__)-5-(6-amino-2-fluoropyridin-3-yl)-2-(hydroxymethyl)-2,3,4,5-tetrahydrofuran-3-ol], C~10~H~13~FN~2~O~3~, is a C-nucleoside with fluorine replacing the O2 carbonyl of deoxycytidine (dC). The furanose ring adopts a C2′-endo conformation, while the orientation of the pyridine ring with respect to the sugar group is anti. The C-glycosidic bond torsion angle χ is anti [−121.32 (13)°]. The C—C glycosidic bond is 1.4952 (17) Å in length, while the C—F bond length is 1.3463 (16) Å.

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1-(1,1-Dioxo-3′-de­oxy-2,3,5,6-tetra­hyd
1-(1,1-Dioxo-3′-de­oxy-2,3,5,6-tetra­hydro-1,4-oxathiine-β-d-ribofuranos­yl)uracil: a bicyclic nucleoside analogue
✍ Sun, Jing-Bo ;Yang, Hua ;Wu, Jin-Chang 📂 Article 📅 2007 🏛 International Union of Crystallography 🌐 English ⚖ 216 KB

In the title compound, C 11 H 14 N 2 O 7 S, the furanose ring adopts a 3 0 -endo,4 0 -exo conformation 4 T 3 . The orientation of the pyrimidine ring with respect to the sugar group is anti. The crystal packing is stabilized by intermolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds.