Stereoselective synthesis and X-ray structure of 1-(4-O-benzyl-1,5- anhydro-2,3-dideoxy-D-arabino-hex-1-enitol-3-yl)-4-methoxy-1H-pyrimidin-2-one

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 3, 2000, Pages 629-635

  Sugimura, Hideyuki ^a,b  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

^b NOGUCHI INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 O BENZYL 1,5 ANHYDRO 2,3 DIDEOXY DEXTRO ARABINO HEX 1 ENITOL 3 YL) 4 METHOXY 1H PYRIMIDIN 2 ONE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HYDROLYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0033999901     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008035013     Document Type: Article

References (17)

1. (a) Leutzinger, E. E.; Robins, R. K.; Townsend, L. B. Tetrahedron Lett., 1968, 4475-4478.
2. (b) ibid. 1970, 3751-3754.
3. (c) Leutzinger, E. E.; Meguro, T.; Townsend, L. B.; Schuman, D. A.; Schweizer, M. P.; Stewart, C. M.; Robins, R. K. J. Org. Chem., 1972 37, 3695-3703.
4. Ferrier, R. J.; Ponpipom, M. M. J. Chem. Soc. C, 1971, 553-559.
5. Kondo, T.; Nakai, H.; Goto, T. Tetrahedron, 1973 29, 1801-1806.
6. Fuertes, M.; García-Munoz, G.; de Las Heras, F. G.; Madronero, R.; Stud, M. Tetrahedron, 1972 28, 4099-4112.
7. Ueda, T.; Watanabe, S.-I., Chem. Pharm. Bull., 1985 33, 3689-3695.
8. Herscovici, J.; Montserret, R.; Antonakis, K. Carbohydr. Res., 1988 176, 219-229.
9. Baud, M.-V.; Chavis, C.; Lucas, M.: Imbach, J.-L., Tetrahedron, 1991 47, 9993-10002.
10. (a) Sujino, K.; Sugimura, H. Chem. Lett., 1993, 1187-1190.
11. (b) Sujino, K.; Sugimura, H. Tetrahedron Lett., 1994 35, 1883-1886.
12. (c) Sugimura, H.; Motegi, M.; Sujino, K. Nucleosides Nucleotides, 1995 14, 413-416.
13. (d) Sugimura, H.; Sujino, K. Nucleosides Nucleotides, 1998 17, 53-63.
14. Sujino, K.; Sugimura, H. J. Chem. Soc., Chem. Commun., 1994, 2541-2542.
15. For details of the experimental procedure, see ref. 8d.
16. Dunkerton, L. V.; Adair, N. K.; Euske, J. M.; Brady, K. T.; Robinson, P. D. J. Org. Chem., 1988 53, 845-850. Also see, Babu, B. S.; Balasubramanian, K. K. Tetrahedron Lett., 1999 40, 5777-5778.
17. Dunkerton, L. V.; Adair, N. K.; Euske, J. M.; Brady, K. T.; Robinson, P. D. J. Org. Chem., 1988 53, 845-850. Also see, Babu, B. S.; Balasubramanian, K. K. Tetrahedron Lett., 1999 40, 5777-5778.