Acyl carbamate directing groups in nucleoside synthesis: Applications in the synthesis of 2′-deoxy-5-ethyl-4′-thiouridine

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1867-1870

  Shaw Ponter, Sue ^a   Mills, Gail ^a   Robertson, Mark ^b   Bostwick, Roy D ^a   Hardy, George W ^a   Young, Robert J ^a,c  

^a Department of Medicinal Chemistry ^*  (United Kingdom)

^b Chemical Development   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HERPES; HERPESVIRIDAE;

2' DEOXY 5 ETHYL 4' THIOURIDINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029925252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00138-4     Document Type: Article

References (15)

1. a) Rahim, S.G., Trivedi, N, Hardy, G.W., Mills, G., Littler, E., Purifoy, D.J.M., Dyson, M.R., Coc, P.L., Basnak, I., Whale, R.F., and Walker, R.T., Presented at the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 4-7th Oct 1994, session 102, abstract H49; Walker, R.T., Dyson, M.R., Whale, R.F., Coe, P.L., Ibid. abstract H51; Littler, E., Lowe, D., Collins, P., Snowden, B.W., Ertl, P., and Alderton, W., Ibid. abstract H53.
2. a) Rahim, S.G., Trivedi, N, Hardy, G.W., Mills, G., Littler, E., Purifoy, D.J.M., Dyson, M.R., Coc, P.L., Basnak, I., Whale, R.F., and Walker, R.T., Presented at the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 4-7th Oct 1994, session 102, abstract H49; Walker, R.T., Dyson, M.R., Whale, R.F., Coe, P.L., Ibid. abstract H51; Littler, E., Lowe, D., Collins, P., Snowden, B.W., Ertl, P., and Alderton, W., Ibid. abstract H53.
3. a) Rahim, S.G., Trivedi, N, Hardy, G.W., Mills, G., Littler, E., Purifoy, D.J.M., Dyson, M.R., Coc, P.L., Basnak, I., Whale, R.F., and Walker, R.T., Presented at the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 4-7th Oct 1994, session 102, abstract H49; Walker, R.T., Dyson, M.R., Whale, R.F., Coe, P.L., Ibid. abstract H51; Littler, E., Lowe, D., Collins, P., Snowden, B.W., Ertl, P., and Alderton, W., Ibid. abstract H53.
4. b) Rahim, S.G., Trivedi, N, Bogunovic-Batchelor, M.V., Hardy, G.W., Mills, G., Selway, J.W.T., Snowden, B.W., Littler, E., Coe, P.L., Basnak, I., Whale, R.F., and Walker, R.T., J. Med. Chem., in press.
5. a) Secrist, J.A. III, Riggs, R.M., Tiwari, K.N., and Montgomery, J.A., J. Med. Chem., 1991, 34, 2361-2366;
6. b) Dyson, M.R., Coe, P.L., and Walker, R.T., J. Med Chem., 1991, 34, 2782-2786;
7. c) Uenishi, J., Motoyama, M., and Takakashi, K., Tetrahedron Asym., 1994, 5, 101-110;
8. d) Jandhu, K.S. and Selwood, D.L., J. Org. Chem., 1995, 60, 5170-5173.
9. Young, R.J., Shaw-Ponter, S., Hardy, G.W., and Mills, G., Tetrahedron Lett., 1994, 35, 8687-8690.
10. Dyson., M.R., Coe, P.L., and Walker, R.T., J. Chem Soc., Chem. Commun., 1991, 741-742; Carbohydrate Research, 1991, 216, 237-248.
11. Dyson., M.R., Coe, P.L., and Walker, R.T., J. Chem Soc., Chem. Commun., 1991, 741-742; Carbohydrate Research, 1991, 216, 237-248.
12. 2Si requires C, 67.36; H, 6.12; N, 2.18%.
13. 1H NMR peaks due to the 1′ protons at 6.33 ppm (dd, J = 7.9 and 2.4 Hz) for the ct-anomer and 6.50 ppm (dd, J = 10.1 and 6.2 Hz) for the β-anomer.
14. Compounds (7) and (8) were produced from commercially available para-toluenesulphonyl isocyanate and trichloromethyl isocyanate respectively. Acyl isocyanates used to produce compounds (9) to (13) were prepared as toluene solutions in situ by refluxing the appropriate acid chloride with silver cyanate for 30 minutes and decanting aliquots from the cooled, settled, suspension.
15. An 83% yield of (10) was isolated after column chromatography from a 1 mmol scale reaction. The other carbamates gave coupled products in comparable yields, which was evident from hplc/NMR analysis.