Synthesis of oligonucleotides containing 3'-alkyl amines using isobutyryl protected deoxyadenosine phosphoramidite

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3123-3126

  McMinn, Dustin L ^a   Greenberg, Marc M ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030999270     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00568-6     Document Type: Article

References (16)

1. Matray, T. J.; Greenberg, M. M. J. Am. Chem. Soc. 1994, 116, 6931.
2. (a) McMinn, D. L.; Greenberg, M. M. Tetrahedron 1996, 52, 3827.
3. (b) Yoo, D. J.; Greenberg, M. M. J. Org. Chem. 1995, 60, 3358.
4. (a) Pirrung, M. C.; Fallon, L.; Lever, D. C.; Shuey, S. W. J. Org. Chem. 1996, 61, 2129.
5. (b) Pirrung, M. C.; Bradley, J-C. J. Org. Chem. 1995, 60, 6270.
6. (a) Venkatesan, H.; Greenberg, M. M. J. Org. Chem. 1996, 61, 525.
7. (b) Schulhof, J. C.; Molko, D.; Teoule, R. Tetrahedron Lett. 1987, 28, 51.
8. (a) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123.
9. (b) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 1925.
10. (c) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223.
11. McMinn, D. L.; Greenberg, M. M. (manuscript in preparation).
12. While this letter was in preparation, 9 has become offered as a phosphoramidite compatible with 1 (The Glen Report 1996, 9, 2.). The synthesis of 9, its compatibility with primary alkyl amines, and its general utility in oligonucleotide synthesis have not been reported.
13. 3CN; 0-100% B, 30 min, linearly; 1.0 mL/min. Ret. time: 5a, 21.6 min; 5b, 23.4 min; 6, 18.9 min.
14. Gao, X.; Gaffney, B. L.; Hadden, S.; Jones, R. A. J. Org. Chem. 1986, 51, 755.
15. -1.
16. 14, 6.6 min.