A new route to oligodeoxynucleoside phosphoramidates (P-NH2)

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5285-5288

  Laurent, Alain ^a   Debart, Françoise ^a   Rayner, Bernard ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; NUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHOTOLYSIS; TECHNIQUE; ULTRAVIOLET IRRADIATION;

EID: 0030855786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01153-2     Document Type: Article

References (19)

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5. Morvan, F.; Rayner, B.; Imbach, J.-L. α-Oligodeoxynucleotides. In Methods in Molecular Biology. Protocols for Oligonucleotides and Analogs; Agrawal, S. Ed.; Human Press Inc.: Totowa, 1993; Vol. 20; pp. 261-283.
6. Froehler, B. C. Tetrahedron Lett. 1986, 27, 5575-5578.
7. 19 with 50% yield, from 2-nitrobenzaldehyde which first reacted with methoxyamine hydrochloride to afford the transient cristalline oxime-ether.The oxime was then reduced by diborane/THF at 0°C to give the desired amine which was further distillated before use (bp 110-112°C, 3 mm Hg). 2-nitrobenzylamine HCl can be also purchased from Karl Industries, Inc. Aurora, OHIO, USA.
8. Jager, A.; Levy, M. J.; Hecht, S. M. Biochemistry 1988, 27, 7237-7246.
9. +calc. 675.19, found 675.2
10. Walker, J. W.; Reid, G. P.; McCray, J. A.; Trentham, D. R. J. Am. Chem. Soc. 1988, 110, 7170-7177.
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12. + calc. 540.16, found 540.10
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14. Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1986, 27, 469-472.
15. + calc. 675.19, found 674.90
16. +
17. Reynolds, M. A.; Hogrefe, R. I.; Jaeger, J. A.; Schwartz, D. A.; Riley, T. A.; Marvin, W. B.; Daily, W. J.; Vaghefi, M. M.; Beck, T. A.; Knowles, S. K.; Klem, R. E.; Arnold Jr, L. J. Nucl. Acids Res. 1996, 24, 4584-4591.
18. Oligo 16 MALDI-TOF MS (positive mode): 3544 (3548 calc. for M+H)
19. Feuer, H., Braunstein, D. M. J. Org. Chem. 1969, 34, 1817-1821.