Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7455-7458

  Nowak, Ireneusz ^a   Conda Sheridan, Martin ^a   Robins, Morris J ^a  

^a N243 Eyring Science Center   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTAMINATION; DERIVATIVES; HEATING; METHANOL; ORGANIC ACIDS;

ARYLCARBOXYLIC ACID DERIVATIVES; N,O-PERACYLATED NUCLEOSIDES; N-DEACYLATION;

NUCLEIC ACIDS;

ACID; ADENOSINE; CYTIDINE; METHANOL; NUCLEIC ACID; NUCLEOSIDE; REAGENT;

ARTICLE; CONTAMINATION; DEACYLATION; HEAT TREATMENT; HEATING; NUCLEIC ACID SYNTHESIS; TEMPERATURE DEPENDENCE;

ACYLATION; HEAT; METHANOL; NUCLEOSIDES;

EID: 24144470767     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051256w     Document Type: Article

References (24)

1. Paper 126 is: Janeba, Z.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Robins, M. J. J. Med. Chem. 2005, 48, 4690-4696.
2. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1999.
3. (a) Asakura, J.-i. Nucleosides Nucleotides 1993, 12, 701-711 and references therein.
4. (b) Ishido, Y.; Sakairi, N.: Okazaki, K.; Nakazaki, N. J. Chem. Soc., Perkin Trans, 1 1980, 563-573.
5. Singh, H. K.; Cote, G. L.; Sikorski. R. S. Tetrahedron Lett. 1993, 34, 5201-5204.
6. Igolen, J.; Morin, C. J. Org. Chem. 1980, 45, 4802-4804.
7. Vorbrüggen, H.; Ruh-Pohlenz, C. Org. React. 2000, 55, 1-630.
8. Liu, J.; Robins, M. J. Org. Lett. 2005, 7, 1149-1151.
9. Holy, A. Collect. Czech. Chem. Commun. 1979, 44, 1819-1827.
10. Beranek, J.; Pitha, J. Collect. Czech. Chem. Commun. 1964, 29, 625-633.
11. Kierzek, R.; Ito, H.; Bhatt, R.; Itakura, K. Tetrahedron Lett. 1981, 22, 3761-3764.
12. Also indicated by the moderate yields and necessity for further purifications reported by: (a) Reist, E. J.; Calkins, D. F.; Fisher, L. V.; Goodman, L. J. Org. Chem. 1967, 33, 1600-1603.
13. (b) Nair, V.; Chamberlain, S. D. Synthesis 1984, 401-403.
14. (a) Rammler, D. H.; Khorana, H. G. J. Am. Chem. Soc. 1962, 84, 3112-3122.
15. (b) Schaller, H.; Weimann, G.; Lerch, B.; Khorana, H. G. J. Am. Chem. Soc. 1963, 85, 3821-3827.
16. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316-1319.
17. Lindell, S. D.; Moloney, B. A.; Hewitt, B. D.; Earnshaw, C. G.; Dudfield, P. J.; Dancer, J. E. Bioorg. Med. Chem. Lett. 1999, 9, 1985-1990.
18. Robins, M. J.; Naik, S. R. Biochemistry 1971, 10, 3591-3597.
19. Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H.; Jones, K. M. Data for Biochemical Research; Oxford University Press: New York; 1969.
20. Ikehara, M.; Fukui, T.; Uesugi, S. J. Biochem. 1974, 76, 107-115.
21. Buchanan, J. G.; Stobie, A.; Wightman, R. H. Can. J. Chem. 1980, 58, 2624-2627.
22. Wiley, P. F.; Johnson, J. H.; Hanze A. R. J. Antibiotics 1976, 29, 720-727. The site of N-acetylation (N4) and signal integration (5.3-5.9 ppm range) were reported incorrectly for 8a.
23. Kozai, S.; Yorikane, A.; Maruyama, T. Nucleosides Nucleotides Nucleic Acids 2001, 20, 1523-1531.
24. Saladino, R.; Mincione, E.; Crestini, C.; Mezzetti, M. Tetrahedron 1996, 52, 6759-6780.