Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

An Efficient One-pot N-Acylation of Deoxy- and Ribo-cytidine Using Carboxylic Acids Activated in situ with 2-Chloro-4,6-dimethoxy-1,3,5-triazine

  • Rode, Ambadas B. (Department of Chemistry, Kongju National University) ;
  • Son, Sang-Jun (College of BioNano Technology, Kyungwon University) ;
  • Hong, In-Seok (Department of Chemistry, Kongju National University)
  • Received : 2010.05.02
  • Accepted : 2010.05.14
  • Published : 2010.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223. https://doi.org/10.1016/S0040-4020(01)88752-4
  2. Marcuccio, S. M.; Elmes, B. C.; Holan, G.; Middleton, E. J. Nucleosides & Nucleotides 1992, 11, 1695. https://doi.org/10.1080/07328319208017816
  3. Schaller, H.; Weimann, G.; Lerch, B.; Khorana, H. G. J. Am. Chem. Soc.1963, 85, 3821. https://doi.org/10.1021/ja00906a021
  4. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316. https://doi.org/10.1021/ja00369a029
  5. Uznanski, B.; Grajkowski, A.; Wilk, A. Nucl. Acids Res. 1989, 17, 4863. https://doi.org/10.1093/nar/17.12.4863
  6. Sinha, N. D.; Davis, P.; Schultze, L. M.; Upadya, K. Tetrahedron Lett. 1995, 36, 9277. https://doi.org/10.1016/0040-4039(95)02011-D
  7. Bhat, B.; Sanghvi,Y. S. Tetrahedron Lett. 1997, 38, 8811. https://doi.org/10.1016/S0040-4039(97)10423-3
  8. Bhat, V.; Ugarkar, B. G.; Sayeed, V. A.; Grimm, K.; Kosora, N.; Domenico, P. A.; Stocker, E. Nucleosides & Nucleotides 1989, 8, 179 https://doi.org/10.1080/07328318908054166
  9. Reid, A. K.; McHugh, C. J.; Richie, G.; Graham, D. Tetrahedron Lett. 2006, 47, 4201. https://doi.org/10.1016/j.tetlet.2006.04.079
  10. Mishra, R.; Mishra ,S.; Diwedi, V.; Misra, K. Nucleic Acids Symposium Series 2006, 50(1), 7. https://doi.org/10.1093/nass/nrl004
  11. De Luca, L.; Giacomelli, G.; Porcheddu , A. J. Org. Chem. 2002, 67, 6272. https://doi.org/10.1021/jo025960d
  12. Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett. 2000, 2, 273.
  13. Falorn i, M.; Giacomelli, G.; Porcheddu, A.; Taddei, M. J. Org. Chem. 1999, 64, 8962. https://doi.org/10.1021/jo991112f
  14. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395. https://doi.org/10.1016/S0040-4039(99)00734-0
  15. Kaminski, Z. J. Biopolimers (Pept.Sci) 2000, 55, 140-164. https://doi.org/10.1002/1097-0282(2000)55:2<140::AID-BIP40>3.0.CO;2-B
  16. Kaminski, Z. J.; Paneth, P.; Rudzinski, J. J. Org. Chem. 1998, 63, 4248-4255. https://doi.org/10.1021/jo972020y
  17. Kaminski, Z. J.; Kolesinska, B.; Kaminska, J. E.; Gora, J. J. Org. Chem. 2001, 66, 6276. https://doi.org/10.1021/jo0101499
  18. De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534. https://doi.org/10.1021/jo015524b
  19. De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2001, 3, 1519. https://doi.org/10.1021/ol015840c
  20. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 2331. https://doi.org/10.1016/S0040-4039(03)00251-X
  21. Bandgar, B. P.; Pandit, S. S. Tetrahedron Lett. 2003, 44, 3855. https://doi.org/10.1016/S0040-4039(03)00684-1
  22. Sinha, N. D.; Davis, P.; Usman, N.; Perez, J.; Hodge, R.; Kremsky, J.; Casale, R. Biochimie 1993, 75, 13. https://doi.org/10.1016/0300-9084(93)90019-O

Cited by

  1. ChemInform Abstract: An Efficient One‐Pot N‐Acylation of Deoxy‐ and Ribo‐cytidine Using Carboxylic Acids Activated in situ with 2‐Chloro‐4,6‐dimethoxy‐1 vol.41, pp.48, 2010, https://doi.org/10.1002/chin.201048206
  2. Gelation properties of self-assembling N-acyl modified cytidine derivatives vol.2, pp.47, 2010, https://doi.org/10.1039/c4tb01375a
  3. Nucleobase Protection of Deoxyribo‐ and Ribonucleosides vol.69, pp.1, 2010, https://doi.org/10.1002/cpnc.32
  4. Enabled Process To Synthesize Monobactam 1 for Early Development vol.23, pp.11, 2010, https://doi.org/10.1021/acs.oprd.9b00374