Synthesis of 5-formyluridines

Nucleosides and Nucleotides

Volumn 16, Issue 10-11, 1997, Pages 2019-2024

  Selvidge III, Sidney D ^a   Jang, James ^a   Ray, Partha S ^a  

^a University of Memphis   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 FORMYL 2',3' O ISOPROPYLIDENEURIDINE; 5 FORMYL 2',3',5' TRI O ACETYLURIDINE; ACETIC ANHYDRIDE; ACETONE; ALKYNE; STYRENE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; CATALYSIS; COUPLING FACTOR; DRUG EFFECT; DRUG POTENCY; DRUG SYNTHESIS; METHODOLOGY; REVIEW;

EID: 0031452360     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319708002552     Document Type: Review

References (12)

1. (a) De Clercq, E. in Approaches to Antiviral Agents, Ed. Harnden, M. R., Mc.Millan, New York, 1985, 57-99;
2. (b) De Clercq, E. Pure Appl. Chem., 1983, 55, 623.
3. (a) Goodchild, J.; Porter, R. A.; Raper, R. H.; Sim, I. S.; Upton, R. M.; Viney, J.; Wadsworth, H. J. J. Med. Chem., 1983, 26, 1252;
4. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides and Nucleotides , 1991,10, 1615.
5. Imia, K.-L; Hono, M., Chem. Pharm. Bull., 1965, 13, 1.
6. (a) Scheit, K. H. Chem. Ber., 1966, 99, 3884;
7. (b) Armstrong, V. W.; Eckstein, F. Nucleic Acid Res., Suppl. 1, 1975, 97;
8. (c) Armstrong, V. W.; Witzel, G.; Eckstein, F. "Nucleic Acid Chemistry; Improved and New Synthetic Procedures, Methods, and Techniques, Part 3," Townsend, L. B.; Tipson, R. S. Eds.; John Wiley & Sons, New York, 1986, pp 65-68.
9. Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides and Nucleotides, 1992, 11, 1425.
10. The synthesis of 5-formyl-2′,3′,5′-tri-O-acetyluridine (5) has been reported recently from 5-formyluracil via silylation with HMDS followed by reaction with β-D-ribofuranose 1,2,3,5-tetraacetate in the presence of TMS triflate: El-Barbary, A. A.; Khodair, A. I.; Pedersen, E. B.; Nielsen, C. Liebigs Ann. Chem., 1994, 619.
11. Robins, M. J.; Barr, P. J.; Giziewicz, J. Can. J. Chem., 1982, 60, 554.
12. The synthesis of (E)-5-styryluridine (3) has been reported (in 39% yield) via a Heck reaction between 5-chloromercuriuridine and styrene: Bergstrom, D. E.; Ogawa, M. K. J. Am. Chem. Soc., 1978, 100, 8106.