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Use of the 2-(2-Pyridyl)Ethyl Protecting Group in the Synthesis of DNA Fragments via Phosphoramidite Intermediates

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Pages 293-296 | Published online: 05 Dec 2006

References

  • Beaucage , S. L. and Caruthers , M. H. 1981 . Tetrahedron Lett. , 22 : 1859 McBride, L. J.; Caruthers, M. H. 1983, 24, 145; Adam, S. P.; Kavka, K. S.; Wykes, E. J. Holder, S. B., Galuppi, G. R. J. Am. Chem. Soc. 1983, 105, 661; Döper, T., Winnacker, E. L. Nucleic Acids Res. 1983, 11, 2575.
  • Barone , A. D. , Tang , J. Y. and Caruthers , M. H. 1984 . Nucleic Acid Res. , 12 : 4061 Beaucage, S. L. Tetrahedron Lett. 1984., 25., 375; Lee, H‐J., Moon, S‐H. Chem. Lett. 1984. 1229; Jager, A., Engels, J. Tetrahedron Lett. 1984, 25, 1437.
  • Letsinger , R. L. , Groody , E. P. and Tanaka , T. 1982 . J. Am. Chem. Soc , 104 : 6805 Sinha, N. D., Biernat, J., Köbster, H. Tetrahedron Lett. 1983, 24., 5843; Claesen, C; Tesser, G. I., Marugg, J. E., van der Marel, G. A., van Boom, J. H. Tetrahedron Lett. 1984, 25., 1307; Fourrey, J. L., Varenne, J. Tetrahedron Lett. 1984, 25., 4511; Schwarz, M. W., Pfleiderer, W. Tetrahedron Lett. 1984, 25., 5513; Marugg, J. E., Dreef, C. E., van der Marel, G. A., van Boom, J. H. Recl. Trav. Chem. Pays‐Bas 1984, 103, 97.
  • King , R. B. and Sundaram , P. M. J. 1984 . Am. Chem. Soc. , 49 : 1784 3 was prepared in high yield by a modification of the procedure of King, and it is much more stable than various phosphorodi‐chloridites.
  • 4 could not be distilled as it undergoes thermal decomposition, but it was sufficiently pure (ca. 95%, 6129.3 ppm) for synthetic purposes.In this case, only bis‐(diisopropylamino)‐chlorophosphine was detected as the only impurity by 31pNMR (ca. 3%, δ 140.0 ppm).
  • Diisopropylammonium tetrazolide, 4,5‐dichloroimidazole, collidine hydrochloride, and 1H‐tetrazole were tested as catalysts in the preaparation of 2a and the result was obtained with diisopropylammonium tetrazolide.
  • 31pNMR Spectra data of phosphoramidites. 2b: 6147.5,6147.2; 2c: 6147.6,6147.4; 2d: 61 47.3, 6U6.5 .
  • The d‐TpT (7a) was completely degraded with Nuclease P1 to d‐T and d‐pT in ratios of 1.00:1.01. The unprotected dinucleotides 7b‐d were isolated in 81–95% yields.
  • Goldstein , A. , Tachibana , S. , Lowney , L. I. , Hunkapiller , M. and Hood , L. Proc. Natl. Acad. Sci. U.S.A.. Tachibana, S., Araki, K., Ohya, S. Yoshida, S. Nature. 1982, 29, 339; Ohshima, S. Morita, K.; Takaku, H. Chem. Pharm. Bull. 1984, 32, 4690.
  • Köster , H. , Stumpe , A. and Wolter , A. 1983 . Tetrahedron Lett. , 24 : 747
  • Matteucci , M. D. and Caruthers , M. H. 1981 . J. Am. Chem. Soc. , 102 : 3185
  • Takaku , H. , Morita , K. and Smiuchi , T. 1983 . Chem. Lett. , : 1661
  • Takaku , H. , Kamaike , K. and Tsuchiya , H. 1984 . J. Org. Chem. , 49 : 51

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