Selective deacylation of peracylated ribonucleosides

Tetrahedron Letters

Volumn 50, Issue 15, 2009, Pages 1751-1753

  Rigoli, Jared W ^a   Østergaard, Michael E ^a   Canady, Kirsten M ^a   Guenther, Dale C ^a   Hrdlicka, Patrick J ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

Acylation; Deprotection; Guanidinium nitrate; LNA; Protecting groups

Indexed keywords

GUANIDINE DERIVATIVE; METHANOL; METHYL CHLORIDE; NITRIC ACID DERIVATIVE; NUCLEIC ACID BASE; RIBONUCLEOSIDE DERIVATIVE;

ACYLATION; ARTICLE; DEACYLATION; DEPROTECTION REACTION; MOLECULAR STABILITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 60649085395     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.147     Document Type: Article

References (29)

1. Herdewijn P. Modified Nucleosides in Biochemistry, Biotechnology and Medicine. 1st ed. (2008), Wiley
2. Duca M., Vekhoff P., Oussedik K., Halby L., and Arimondo P.B. Nucleic Acids Res. 36 (2008) 5123-5138
3. Kurreck J. Eur. J. Biochem. 270 (2003) 1628-1644
4. Bumcrot D., Manoharan M., Koteliansky V., and Sah D.W.Y. Nat. Chem. Biol. 2 (2006) 711-719
5. Asseline U. Curr. Opin. Chem. 10 (2006) 491-518
6. Prasad A.K., Kumar V., Malhotra S., Ravikumar V.T., Sanghvi Y.S., and Parmar V.S. Bioorg. Med. Chem. 13 (2005) 4467-4472
7. Kumar V., Parmar V.S., and Malhotra S.V. Tetrahedron Lett. 48 (2007) 809-812
8. Nowak I., Conda-Sheridan M., and Robins M.J. J. Org. Chem. 70 (2005) 7455-7458
9. Nowak I., Jones C.T., and Robins M.J. J. Org. Chem. 71 (2006) 3077-3081 and Ref. 9 therein
10. Bhat V., Ugarkar B.G., Sayeed V.A., Grimm K., Kosora N., Domenico P.A., and Stocker E. Nucleosides Nucleotides 8 (1989) 179-183
11. Ti G.S., Gaffney B.L., and Jones R.A. J. Am. Chem. Soc. 104 (1982) 1316-1319
12. Zhu X.-F., Williams H.J., and Scott A.I. Synth. Commun. 33 (2003) 1233-1243
13. Rammler D.H., and Khorana H.G. J. Am. Chem. Soc. 84 (1962) 3112-3122
14. Saito Y., Nyilas A., and Agrofoglio L.A. Carbohydr. Res. 331 (2001) 83-90
15. Maguire A.R., Hladezuk I., and Ford A. Carbohydr. Res. 337 (2002) 369-372
16. Neilson T., and Werstjuk E.S. Can. J. Chem. 49 (1971) 493-499
17. Hrdlicka P.J., Kumar T.S., and Wengel J. Chem. Commun. (2005) 4279-4281
18. Kumar T.S., Madsen A.S., Wengel J., and Hrdlicka P.J. J. Org. Chem. 71 (2006) 4188-4201
19. Kumar T.S., Wengel J., and Hrdlicka P.J. Chem. Biol. Chem. 8 (2007) 1122-1125
20. Kumar T.S., Madsen A.S., Østergaard M.E., Wengel J., and Hrdlicka P.J. J. Org. Chem. 73 (2008) 7060-7066
21. Kumar, T. S.; Madsen, A. S.; Østergaard, M. E.; Sau, S. P.; Wengel, J.; Hrdlicka, P. J. J. Org. Chem. 2009, 74, 1070-1081.
22. Babu B.R., Raunak, Poopeiko N.E., Juhl M., Bond A.D., Parmar V.S., and Wengel J. Eur. J. Org. Chem. (2005) 2297-2321
23. Matsuda A., Yasuoka J., Sasaki T., and Ueda T. J. Med. Chem. 34 (1991) 999-1002
24. Sekine M. J. Org. Chem. 54 (1989) 2321-2326
25. Ellervik U., and Magnusson G. Tetrahedron Lett. 38 (1997) 1627-1628
26. See note 37 in Ref. 17b.
27. See Supplementary data.
28. Kamaike K., Uemura F., Yamakage S., Nishino S., and Ishido Y. Nucleosides Nucleotides 6 (1987) 699-736
29. Nishino S., Takamura H., and Ishido Y. Tetrahedron 42 (1986) 1995-2004