One-pot synthesis of deoxyadenosine 3'-thiophosphates

Tetrahedron Letters

Volumn 39, Issue 41, 1998, Pages 7455-7458

  Szczepanik, Maciej B ^a   Désaubry, Laurent ^a   Johnson, Roger A ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Enzyme inhibitors; Nucleosides; Nucleotides; Thiophosphates

Indexed keywords

2 CHLORO 2 THIO 1,3,2 DIOXAPHOSPHOLANE; ADENOSINE 3' THIOPHOSPHATE DERIVATIVE; ADENOSINE 5' THIOPHOSPHATE DERIVATIVE; ADENYLATE CYCLASE; DEOXYADENOSINE; DEOXYADENOSINE DERIVATIVE; ENZYME INHIBITOR; PHOSPHOROTHIOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEOTIDE METABOLISM; PHOSPHORYLATION; STRUCTURE ANALYSIS;

EID: 0032497673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4039(98)01669-4     Document Type: Article

References (18)

1. 1. Désaubry, L.; Shoshani, I.; Johnson R.A., J. Biol. Chem. 1996, 271, 14028-14034.
2. 2. Johnson, R.A.; Yeung, S-M.H.; Stübner, D.; Bushfield, M.; Shoshani, I., Mol. Pharmacol. 1989, 35, 681-688.
3. 3. Eckstein, F., Angew. Chem. Int. Ed. Engl. 1983, 22, 423-506.
4. 4. Colman, R.F., The Enzymes 1990, 19, 283-321.
5. 5. Mayer A.; Neuenhofer S., Angew. Chem. Int. Ed. Engl. 1994, 33, 1044-1072.
6. 6. McGrath J.C.; Arribas, S.; Daly, C.J., Trends Pharmacol. Sci. 1996, 17, 393-399.
7. 7. Varma, R.S., Synlett. 1993, 621-637.
8. 8. Roelen, H.C.P.F., Kamer, P.C.J., Van den Elst, H., Van der Marel, G.A., Van Boom, J.H., Recl. Trav. Chim. Pays-Bas 1991, 110, 325-331.
9. 9. Thuong, N.T., Chassignol, M., Tetrahedron Lett. 1987, 28, 4157-4160.
10. 10. Baker, G.R, Billington, D.C., Gani, D., Tetrahedron 1991, 47, 3895-3908.
11. 11. Cooke, A.M., Gigg, R., Potter, B.V.L., J. Chem. Soc., Chem. Commun. 1987, 525-1526.
12. 3Cl) δ 4.47-4.62 (m, 4H).
13. 3Cl) δ 4.47-4.62 (m, 4H).
14. 13. Désaubry, L.; Shoshani, I.; Johnson, R.A., Nucleosides & Nucleotides 1995, 14, 1453-1460.
15. 14. Thuong, N.T., Chabrier, P., Bull. Soc. Chim. Fr. 1975, 9-10, 2083-2088.
16. 15. tert-Butylmagnesium chloride (3 mmol) was added dropwise to a solution of 2′,5′-dd-Ado 4a (3 mmol) in the mixture of THF (40 ml) and DMF (3 ml). After 5 min, a solution of 5 (3.75 mmol) in benzene was added and the mixture was stirred at room temperature for an additional 1.5 h. The reaction mixture was concentrated, diluted with 50 ml water and extracted with ethyl acetate. After evaporation of solvent, 6a was dissolved in 30 ml DMSO containing 4 equivalents of NaCN. The solution was stirred overnight under vacuum. Then the mixture was treated for 2 h with 4.5 mmoles of NaOH in 20 ml of EtOH. Final compound 7 was purified on DEAE-Sephadex ion-exchange column using TEAB as an eluent. Isolated triethylammonium salt of 7 was converted to its sodium salt by treatment with 1 M NaI in acetone.
17. 16. Ogilvie, K., Can. J. Chem. 1973, 51, 3799-3807.
18. 6PS: 362.3).