Synthesis of the L-enantiomer of 4′-C-ethynyl-2′-deoxycytidine

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 8, 2001, Pages 1879-1882

  Kohgo, Satoru ^a   Mitsuya, Hiroaki ^b,c   Ohrui, Hiroshi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b KUMAMOTO UNIV SCHOOL OF MEDICINE   (Japan)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

4 C ethynyl 2 deoxycytidine; Anti HIV activity; L configuration nucleosides

Indexed keywords

HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

4' C ETHYNYL 2' DEOXYCYTIDINE; 4'-C-ETHYNYL-2'-DEOXYCYTIDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; COLORING AGENT; DEOXYCYTIDINE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; TETRAZOLIUM; THIAZOLE DERIVATIVE; THIAZOLYL BLUE;

ARTICLE; CELL LINE; DRUG EFFECT; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; HUMAN IMMUNODEFICIENCY VIRUS 1; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STEREOISOMERISM; SYNTHESIS;

ANTI-HIV AGENTS; CELL LINE; COLORING AGENTS; DEOXYCYTIDINE; HIV-1; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; STEREOISOMERISM; TETRAZOLIUM SALTS; THIAZOLES;

EID: 0035431667     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1879     Document Type: Article

References (9)

1. Beach, J. W., Jeong, L. S., Alves, A. J., Pohl, D., Kim, H. O., Chang, C. N., Doong, S. L., Schinazi, R. F., Cheng, Y.-C., and Chu, C. K., Synthesis of enantiomerically pure (2′R,5′S)-(-)-1-[2-(hydroxymethyl)-1,3-oxathiolane-5-yl]cytosine as potent anti-viral agent against hepatitis B virus (HBV) and immunodeficiency virus (HIV). J. Org. Chem., 57, 2217-2219 (1992).
2. Waga, T., Nishizaki, T., Miyakawa, I., Ohrui, H., and Meguro, H., Synthesis of 4′-C-methylnucleosides. Biosci. Biotechnol. Biochem., 57, 1433-1438 (1993).
3. Waga, T., Ohrui, H., and Meguro, H., Synthesis and biological evaluation of 4′-C-methylnucleosides. Nucleosides Nucleotides, 15, 287-304 (1996).
4. Yamaguchi, R., Imanishi, T., Kohgo, S., Horie, H., and Ohrui, H., Syntesis of 4-C-ethynyl-β-D-ribo-pentofuranosyl pyrimidines. Biosci. Biotechnol. Biochem., 63, 736-742 (1998).
5. Ohrui, H., Kohgo, S., Kitano, K., Sakata, S., Kodama, E., Yoshimura, K., Matsuoka, M., Shigeta, S., and Mitusya, H., Syntheses of 4′-C-ethynyl-β-D-arabino-and 4′-C-ethynyl-2′-deoxy-β-D-ribo-pentofuranosylpyrimidines and -purines, and evaluation of their anti-HIV activity. J. Med. Chem., 43, 4516-4525 (2000).
6. Corey, E. J. and Fuchs, P. L., A synthetic method for formyl-ethynyl conversion. Tetrahedron Lett., 36, 3769-3772 (1972).
7. Oikawa, Y., Yoshioka, T., and Yonemitsu, O., Protection of hydroxy groups by intramolecular oxidative foemation of methoxybenzylidene acetals with DDQ. Tetrahedron Lett., 23, 889-892 (1982).
8. Robins, M. J., Wilson, J. S., and Hansske, F., Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of ribonucleosides to 2′-deoxynucleosides. J. Am. Chem. Soc., 105, 4059-4065 (1982).
9. Vorbruggen, H., Krolikiewicz, K., and Bennua, B., Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber., 114, 1234-1268 (1981).