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Synthesis and Crystal Structures of O-2′,3′-Cyclic Cyclopentanone and Cyclohexanone Ketals of the Cytostatic 5-Fluorouridine

✍ Scribed by Edith Malecki; Fei Ye; Hans Reuter; Helmut Rosemeyer

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
328 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of two __O‐__2′,3′‐cyclic ketals, i.e., 5 and 6, of the cytostatic 5‐fluorouridine (2), carrying a cyclopentane and/or a cyclohexane ring, respectively, is described. The novel compounds were characterized by ^1^H‐, ^19^F‐, and ^13^C‐NMR, and UV spectroscopy, as well as by elemental analyses. Their crystal structures were determined by X‐ray analysis. Both compounds 5 and 6 show an anti‐conformation at the N‐glycosidic bond which is biased from +ac to +ap compared to the parent nucleoside 2. The sugar puckering is changed from ^2′^E to ~3′~E going along with a reduction of the puckering amplitude τ~m~ by ca. 10–13° due to the ketalization. The conformation about the sugar exocyclic bond C(4′)C(5′) of 5 and 6 remains unchanged, i.e., g^+^, compared with compound 2.

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O-2′,3′-Ketal-Nucleolipids of the Cytost
O-2′,3′-Ketal-Nucleolipids of the Cytostatic 5-Fluorouridine: Synthesis, Lipophilicity, and Acidic Stability
✍ Edith Malecki; Helmut Rosemeyer 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 German ⚖ 303 KB

## Abstract The synthesis of a series of cyclic and acyclic __O__‐2′,3′‐ketal derivatives of the cancerostatic 5‐fluorouridine (**2a**) is described. The novel compounds were characterized by ^1^H‐ and ^13^C‐NMR, and UV spectroscopy, as well as by elemental analyses. The lipophilicity values (log _