2-(b-D-Ribofuranosyl)-4-(3-nitrophenylazo)-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one

Hussein F. Zohdi; Abdelfattah Haikal

doi:10.3390/M263

and

Department of Chemistry, Faculty of Science, United Arab Emirates University, P.O.Box 17551 Al-Ain, UAE

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Author to whom correspondence should be addressed.

Molecules2001, 6(12), M263;https://doi.org/10.3390/M263

This article belongs to the Section Molbank Section of Molecules, 1997-2001

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The desired compound 2 was obtained by complete deprotection of the acetylated nucleoside 1 [1] using triethylamine [2]. To a solution of 1 (0.9g, 1.4 mmol) in methanol (25 ml) was added triethylamine (2 ml). The mixture was stirred at room temperature and the reaction was followed by tlc. After complete deprotection (24 hours), the reaction mixture was evaporated and coevaporated with methanol (3 x 30 ml), then chromatographed over silica gel using CH2Cl2/MeOH (92:8 v/v) to give 0.56g (90%) of 2 as yellow powder.

Rf (CH₂C_l2/MeOH, 94/6 v/v): 0.2.

UV (lmax, 95% ethanol): 255, 415.

MS (m/z): 433.

¹H-NMR (250 MHz, DMSO-d6): 3.39-3.54(m, 2H, H-5`, H-5``); 3.82-3.87(m, 1H, H-4`); 4.07(t, 1H, H-3`); 4.36(t, 1H, H-2`); 5.63(d, 1H, H-1`, J1`,2`=4.95); 7.74-8.55(m, 4H, aromatic CH).

¹³C-NMR (75 MHz, DMSO-d₆): 61.92(C-5`), 70.35(C-3`); 71.83(C-2`); 84.80(C-4`); 86.10(C-1`); 111.95, 117.51, 120.66, 121.12, 123.90, 131.04(6 aromatic carbons); 136.63(q, CF₃); 142.71(C-4); 148.54(C-5); 156.06(C-3).

Supplementary Materials

References

Haikal, A.; Zohdi, H.F.; El-Neyadi, S. Molecules 2001, 6, M262. [CrossRef]
Spohr, U.; Lemieux, R. Carbohydr. Res. 1988, 174, 211. [CrossRef] [PubMed]

Sample Availability: Available from the authors.

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