Collect. Czech. Chem. Commun.
2004, 69, 918-932
https://doi.org/10.1135/cccc20040918
Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Pyrimidine C-Nucleoside Analogues
Michal Šála, Hubert Hřebabecký*, Milena Masojídková and Antonín Holý
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
References
1. J. G.: Fortschr. Chem. Org. Naturst. 1983, 44, 243.
2a. T. P., Deeprose R. D., Wolberg G., Stopford C. R., Duncan G. S., Miller R. L., Lim M.-I., Ren W.-Y., Klein R. S.: Biochem. Pharmacol. 1983, 32, 1211.
<https://doi.org/10.1016/0006-2952(83)90274-5>
2b. M. Y., Zuckerman L. B., Sato S., Crabtree G. W., Bogden A. E., Lim M.-I., Klein R. S.: Biochem. Pharmacol. 1984, 33, 1229.
<https://doi.org/10.1016/0006-2952(84)90174-6>
3. J. H., Ciovacco K., Kalaher K., O’Toole T., Keifner R., Dowing M. D., Chu C. K., Watanabe K. A., Wempen I., Fox J. J.: Cancer Res. 1976, 36, 1520.
4a. M., Garcia-Lopez T., Garcia-Munoz E., Stud M.: J. Org. Chem. 1976, 41, 4074.
<https://doi.org/10.1021/jo00888a005>
4b. P. C., Pickering M. V., Allen L. B., Streeter D. G., Camplbell M. T., Witkowski J. T., Sidwell R. W., Robins R. K.: J. Med. Chem. 1977, 20, 256.
<https://doi.org/10.1021/jm00212a014>
5a. I., Van Aerschot A., Toppet S., Snoeck R., Janssen G., Balzarini J., De Clercq E., Herdewijn P.: J. Med. Chem. 1993, 36, 2033.
<https://doi.org/10.1021/jm00066a013>
5b. I., Van Aerschot A., Van Meervelt L., Rozenski J., Wiebe L., Snoeck R., Andrei G., Balzarini J., Claes P., De Clercq E., Herdewijn P.: J. Med. Chem. 1995, 38, 826.
<https://doi.org/10.1021/jm00005a010>
6a. M. J., Rozenski J., Busson R., Herdewijn P.: J. Org. Chem. 1995, 60, 1531.
<https://doi.org/10.1021/jo00111a010>
6b. M. J., Vince R.: Nucleosides Nucleotides 1995, 14, 2061.
<https://doi.org/10.1080/15257779508010724>
6c. M. J., Vince R.: Tetrahedron 1996, 52, 799.
<https://doi.org/10.1016/0040-4020(95)00926-4>
6d. M. J., Vince R.: Tetrahedron 1996, 52, 8969.
<https://doi.org/10.1016/0040-4020(96)00445-0>
6e. N., Ito Y., Shiraishi T., Maruyama T., Sato Y., Kaneko C.: Nucleosides Nucleotides 1996, 15, 631.
<https://doi.org/10.1080/07328319608002411>
6f. S. N., Blaton N., Rozenski J., Balzarini J., De Clercq E., Herdewijn P.: Nucleosides Nucleotides 1996, 15, 867.
<https://doi.org/10.1080/07328319608002133>
6g. Y., Schraml J., De Winter H., Blaton N., Peeters O., Lescrinier E., Rozenski J., Van Aershot A., De Clercq E., Busson R., Herdewijn P.: J. Org. Chem. 1997, 62, 2861.
<https://doi.org/10.1021/jo962204x>
6h. J., Busson R., Blaton N., Rozenski J., Herdewijn P.: J. Org. Chem. 1998, 63, 3051.
<https://doi.org/10.1021/jo972285c>
6i. Y., Rosemeyer H., Esnoef R., Medvedovici A., Wang J., Ceulemans G., Lescrinier E., Hendrix C., Busson R., Saudra P., Seela F., Van Aerschot A., Herdewijn P.: Chem. Eur. J. 1999, 5, 2139.
<https://doi.org/10.1002/(SICI)1521-3765(19990702)5:7<2139::AID-CHEM2139>3.0.CO;2-K>
6j. Wang J., Herdewijn P.: Nucleosides Nucleotides 1999, 18, 591, 593.
6k. J., Herdewijn P.: J. Org. Chem. 1999, 64, 7820.
<https://doi.org/10.1021/jo9908288>
6l. J., Froeyen M., Hendrix C., Andrei G., Snoeck R., De Clercq E., Herdewijn P.: J. Med. Chem. 2000, 43, 736.
<https://doi.org/10.1021/jm991171l>
6m. J., Verbeure B., Luyten I., Lescrinier E., Froeyen M., Hendrix C., Rosemeyer H., Seela F., Van Aershot A., Herdewijn P.: J. Am. Chem. Soc. 2000, 122, 8595.
<https://doi.org/10.1021/ja000018+>
6n. D., Santana L., Uriarte E.: Nucleosides, Nucleotides Nucleic Acids 2001, 20, 1363.
<https://doi.org/10.1081/NCN-100002556>
6o. N., Huet F.: J. Org. Chem. 2001, 66, 583.
<https://doi.org/10.1021/jo001467v>
6p. P., De Clercq E.: Bioorg. Med. Chem. Lett. 2001, 11, 1591.
<https://doi.org/10.1016/S0960-894X(01)00270-0>
6q. K., Halfon P., Pepe G., Camplo M.: Tetrahedron Lett. 2002, 43, 81.
<https://doi.org/10.1016/S0040-4039(01)02107-4>
6r. H., Masojídková M., Holý A.: Collect. Czech. Chem. Commun. 2002, 67, 1681.
<https://doi.org/10.1135/cccc20021681>
6s. H., Masojídková M., Holý A.: Collect. Czech. Chem. Commun. 2004, 69, 435.
<https://doi.org/10.1135/cccc20040435>
7a. N., Haneda T., Kaneko C.: Chem. Pharm. Bull. 1986, 34, 4875.
<https://doi.org/10.1248/cpb.34.4875>
7b. N., Haneda T., Hayasaka E., Watanabe N., Kaneko C.: J. Org. Chem. 1988, 53, 226.
<https://doi.org/10.1021/jo00236a057>
7c. N., Nomura M., Kaneko C.: Heterocycles 1990, 30, 211.
7d. N., Tomura M., Haneda T., Kaneko C.: J. Chem. Soc., Chem. Commun. 1987, 1422.
<https://doi.org/10.1039/c39870001422>
7e. R. C., Dufield P. J., Scopes D. I. C.: J. Chem. Soc., Perkin Trans. 1 1986, 393.
<https://doi.org/10.1039/p19860000393>
7f. T., Kotsubo H., Koizumi T.: Tetrahedron Asymmetry 1991, 2, 1035.
<https://doi.org/10.1016/S0957-4166(00)86154-6>
7g. A. P., Humber D. C., Stoodley R. J.: J. Chem. Soc., Perkin Trans. 1 1993, 57.
<https://doi.org/10.1039/p19930000057>
7h. S., Leuman C., Scheffold R.: Helv. Chim. Acta 1996, 79, 702.
<https://doi.org/10.1002/hlca.19960790312>
7i. B. K., Chu C. K.: Tetrahedron Lett. 1999, 40, 3309.
<https://doi.org/10.1016/S0040-4039(99)00482-7>
7j. B. K., Song G. Y., Chu C. K.: J. Org. Chem. 2001, 66, 4852.
<https://doi.org/10.1021/jo010224f>
8a. H., Masojídková M., Holý A.: Collect. Czech. Chem. Commun. 1998, 63, 2044.
<https://doi.org/10.1135/cccc19982044>
8b. H., Holý A.: Collect. Czech. Chem. Commun. 1999, 64, 1485.
<https://doi.org/10.1135/cccc19991485>
8c. H., Holý A.: Collect. Czech. Chem. Commun. 2000, 65, 395.
<https://doi.org/10.1135/cccc20000395>
8d. H., Holý A.: Collect. Czech. Chem. Commun. 2001, 66, 785.
<https://doi.org/10.1135/cccc20010785>
9a. M., Crotti P., Flippin L. A., Macchia F.: J. Org. Chem. 1991, 56, 7043.
<https://doi.org/10.1021/jo00025a018>
9b. M., Crotti P., Flippin L. A., Macchia F., Pineschi M.: J. Org. Chem. 1992, 57, 1405.
<https://doi.org/10.1021/jo00031a018>
10a. J. A., Cohen N., Arenson K. R.: J. Org. Chem. 1965, 30, 762.
<https://doi.org/10.1021/jo01014a026>
10b. H., Vogel F., Weyerstahl P.: Liebigs Ann. Chem. 1977, 1557.
<https://doi.org/10.1002/jlac.197719770917>
11. K., Ichikawa K., Node M., Fujita E.: J. Org. Chem. 1979, 44, 1661.
<https://doi.org/10.1021/jo01324a017>
12a. M. A., Martin J. C., Smee D. F., Matthews T. R., Verheyden J. P. H.: Nucleosides Nucleotides 1984, 3, 525.
<https://doi.org/10.1080/07328318408081287>
12b. K., Kimura H., Ogawa S.: Bull. Chem. Soc. Jpn. 1989, 62, 1355.
<https://doi.org/10.1246/bcsj.62.1355>
13. Votruba I.: Unpublished results.

