Sensible Improvements Induced by Ionic Liquids in the Reaction of Modified Carbasugars with Bases for the Building of Constrained Carbanucleosides

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2881-2883

  Paoli, M Laura ^a   Piccini, Sonia ^a   Rodriquez, Manuela ^a   Sega, Alessandro ^a  

^a UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC SOLVENTS; REDUCTION; SYNTHESIS (CHEMICAL);

IONIC LIQUIDS; REACTION TIMES;

SUGAR (SUCROSE);

1 BUTYL 3 METHYL IMIDAZOLIUM TETRAFLUOROBORATE; 4 HYDROXY 4 METHYL 2 CYCLOPENTENONE; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BORIC ACID; CARBANUCLEOSIDE DERIVATIVE; HETEROCYCLIC COMPOUND; NUCLEIC ACID BASE; NUCLEOSIDE ANALOG; UNCLASSIFIED DRUG;

ARTICLE; DISSOLUTION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; VAPOR PRESSURE;

EID: 1842638305     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035807z     Document Type: Article

References (25)

1. Ichikawa, E.; Kato, K. Curr. Med. Chem. 2001, 8, 385-423.
2. Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272.
3. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205-8212.
4. Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734-9746.
5. Koole, L. H.; Neidle, S.; Crawford, M. D.; Krayevski, A. A.; Garskaya, G. V.; Sandström, A.; Wu, J.-C.; Chattopadhyaya, J. J. Org. Chem. 1991, 56, 6884-6892.
6. Isono, K. J. Antibiot. 1988, 41, 1711-1739.
7. (a) Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331-2334.
8. (b) Altmann, K.-H.; Imwinkelried, R.; Kesselring, R.; Rihs, G. Tetrahedron Lett. 1994, 35, 7625-7628.
9. (c) Siddiqui, M. A.; Ford, H., Jr.; George, C.; Marquez, V. E. Nucleosides Nucleotides 1996, 15, 235-250.
10. (d) Marquez, V. E.; Rues, P.; Alonso, R.; Siddiqui, M. A.; Shin, K.-J.; George, C.; Niklaus, M. C.; Dai, F.; Ford, H., Jr. Nucleosides Nucleotides 1999, 18, 521-530.
11. Comin, M. J.; Pujol, C. A.; Damonte, E. B.; Rodriguez, J. B. Nucleosides Nucleotides 1999, 18, 2219-2231.
12. Adembri, G.; Giorgi, G.; Lampariello, R. L.; Paoli, M. L.; Sega, A. J. Chem. Soc., Perkin Trans. 1 2000, 2649-2656.
13. Giorgi, G.; Lampariello, L. R.; Minetto, G.; Paoli, M. L.; Riello, V.; Rodriquez, M.; Sega, A. Eur. J. Org. Chem. 2003, 4777-4785.
14. Hua, H. D.; Venkataraman, S.; Chan-Yu-King, R.; Paukstelis, J. V. J. Am. Chem. Soc. 1988, 110, 4741-4748.
15. Agrofoglio, L.; Suhas, E.; Farese, A.; Condor, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670.
16. Lindeström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
17. Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, 2003.
18. (a) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772-3789.
19. (b) Davis, J. H.; Fox, P. A. Chem. Commun. 2003, 1209-1212.
20. Some recent references: (a) Ren, R. X.; Wu, J. X. Org. Lett. 2001, 3, 3727-3728. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278-10279.
21. Some recent references: (a) Ren, R. X.; Wu, J. X. Org. Lett. 2001, 3, 3727-3728. Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278-10279.
22. (b) Judeh, Z. M. A.; Shen, H.-Y.; Chi, B. C.; Feng, L.-C.; Selvasothi, S. Tetrahedron Lett. 2002, 43, 9381-9384.
23. (c) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281-4285.
24. Uzagare, M. C.; Sanghri, Y. S.; Salunkhe, M. M. Green Chem. 2003, 5, 370-372.
25. Dupont, J.; Consorti, C.; Suarez, P. A. Z.; de Souza, R. F. Org. Synth. 2002, 79, 236-243.