Thiosugars, 2: Preparation of 2,3,5-tri-O-benzyl-4-thio-L-arabino- furanosides and the corresponding 4'-thionucleoside analogues

European Journal of Organic Chemistry

Volumn , Issue 3, 1999, Pages 691-696

  Wirsching, Jörn ^a   Voss, Jürgen ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

4 Thiofuranosides; Carbohydrates; NOE measurements; Nucleosides; Reaction mechanisms

Indexed keywords

1 O ACETYL 2,3,5 TRI O BENZYL 4 THIO ARABINO FURANOSE; 1,4 DITHIO ARABINO FURANOSIDE; 2,3,5 TRI O BENZYL 4 THIO ARABINO FURANOSIDE; 4' THIONUCLEOSIDE DERIVATIVE; BIS(TRIMETHYLSILYL)URACIL; FURANOSIDE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; COLUMN CHROMATOGRAPHY; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032803171     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199903)1999:3<691::AID-EJOC691>3.0.CO;2-J     Document Type: Article

References (25)

1. R. L. Whistler, W. E. Dick, T. R. Ingle, R. M. Rowell, B. Urbas, J. Org. Chem. 1964, 29, 3723-3725.
2. M. Bobek, A. Bloch, J. Med. Chem. 1975, 18, 784-787.
3. C. Leydier, L. Bellon, J.-L. Barascut, J. Deydier, G. Maury, H. Pelicano, M. A. El Alaoui, J.-L. Imbach, Nucleosides Nucleotides 1994, 13, 2035-2050.
4. Y.-L. Fu, M. Bobek, J. Org. Chem. 1976, 41, 3831-3834.
5. M. R. Dyson, P. L. Coe, R. T. Walker, Carbohydr. Res. 1991, 216, 237-248.
6. E. J. Reist, D. E. Gueffroy, L. Goodman, J. Am. Chem. Soc. 1964, 86, 5658-5663.
7. L. Bellon, J.-L. Barascut, J.-L. Imbach, Nucleosides Nucleotides 1992, 11, 1467-1479.
8. J. Uenishi, K. Takahashi, M. Motoyama, H. Akashi, T. Sasaki, Nucleosides Nucleotides 1994, 13, 1347-1361.
9. R. T. Walker, Spec. Publ. R. Soc. Chem. 1991, 198, 203-237.
10. C. Leydier, L. Bellon, J.-L. Barascut, F. Morvan, B. Rayner, J.-L. Imbach, Antisense Res. Dev. 1995, 5, 167-174.
11. H. Satoh, Y. Yoshimura, S. Sakata, S. Miura, H. Machida, A. Matsuda, Bioorg. Med. Chem. Lett. 1998, 8, 989-992. We thank Prof. Yoshimura for a reprint of his brand-new publication.
12. E. J. Reist, L. V. Fisher, L. Goodman, J. Org. Chem. 1968, 33, 189-192.
13. S. A. Hartsel, W. S. Marshall, Tetrahedron Lett. 1998, 39, 205-208.
14. Y. Yoshimura, M. Watanabe, S. Sakata, N. Ashida, S. Miyazaki, H. Machida, A. Matsuda, Nucleic Acids Symp. Ser. 1995, 24, 21-22.
15. Y. Yoshimura, M. Watanabe, H. Satoh, N. Ashida, K. Ijichi, S. Sakata, H. Machida, A. Matsuda, J. Med. Chem. 1997, 40, 2177-2183.
16. B. Huang, Y. Hui, Nucleosides Nucleotides 1993, 12, 139-147.
17. K. Blumberg, A. Fuccello, T. van Es, Carbohydr. Res. 1979, 70, 217-232.
18. J. Harness, N. A. Hughes, Chem. Commun. 1971, 811.
19. H. Ait-sir, N.-E. Fahmi, G. Goethals, G. Ronco, B. Tber, P. Villa, D. F. Ewing, G. Mackenzie, J. Chem. Soc., Perkin Trans. 1 1996, 1665-1671.
20. C. Birk, J. Voss, J. Wirsching, Carbohydr. Res. 1997, 304, 239-247.
21. K. K. Andersen, "Stereochemistry and chiroptical properties of the sulphonium group" in The chemistry of the sulphonium group (Ed.: C. J. M. Stirling) in The chemistry of functional groups (Ed.: S. Patai), Wiley, New York, 1981, part 1, p. 229.
22. J. Brånalt, I. Kvarnström, G. Niklasson, S. C. T. Svensson, J. Org. Chem. 1994, 59, 1783-1788.
23. Autorenkollektiv, Organikum, 19th ed., Johann Ambrosius Barth Verlag, Leipzig, 1993, pp. 659-681.
24. M. A. Thomé, M. B. Giudicelli, D. Picq, D. Anker, J. Carbohydr. Chem. 1991, 10, 923-926.
25. 2.