Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8621-8624

  Ozola, Vita ^a   Reese, Colin B ^a   Song, Quanlai ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030592799     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01993-4     Document Type: Article

References (16)

1. 1. Reese, C. B. Tetrahedron 1978, 34, 3143-3179.
2. 2. Beaucage, S. L.; Caruthers, M. H. Tetrahedron Lett. 1981, 22, 1859-1862.
3. 3. Garegg, P. J.; Regberg, T.; Stawinski, J.; Strömberg, R. Chemica Scripta 1985, 25, 280-282.
4. 4. Liu, X.; Reese, C. B. J. Chem. Soc., Perkin Trans, 1 1995, 1685-1694.
5. 5. For recent reviews on the H-phosphonate approach, see (a) Froehler, B. C. in Methods in Molecular Biology, Vol. 20, Protocols for Oligonucleotides and Analogs, Agrawal, S., Ed., Humana, Totowa, 1993, pp 63-80, and
6. (b) Stawinski, J. in Handbook of Organophosphorus Chemistry, Engel, R., Ed., Dekker, New York, 1992, pp 377-434.
7. 6. Hammond, P. R. J. Chem. Soc., 1962, 2521-2522.
8. P,H 607.7).
9. 8. Froehler, B. C.; Matteucci, M. D. Tetrahedron Lett. 1986, 27, 469-472.
10. 9. Westheimer, F. H.; Huang, S.; Covitz, F. J. Am. Chem. Soc. 1988, 110, 181-185.
11. 31P NMR and HPLC data are indicated in Table 1.
12. 11. In the phosphotriester approach, we found 12,13 that it was advisable to protect guanine residues both with a 2-N-acyl and a 6-O-aryl group. As it is not yet clear whether such double protection is desirable in the H-phosphonate approach, we have prepared two 2′-deoxyguanosine H-phosphonate building blocks 2; B = 11 and 2; B = 12 with singly-and doubly-protected guanine residues, respectively.
13. 12. Jones, S. S.; Reese, C. B.; Sibanda, S.; Ubasawa, A. Tetrahedron Lett. 1981, 22, 4755-4758.
14. 13. Reese, C. B.; Skone, P. A. J. Chem. Soc., Perkin Trans, 1 1984, 1263-1271.
15. 14. Froehler, B. C.; Ng, P. G.; Matteucci, M. D. Nucleic Acids Res. 1986, 74, 5399-5407.
16. 15. Marugg, J. E.; Tromp, M.; Kuyl-Yeheskiely, E.; van der Marel, G.A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 2661-2664.