Electrophilic addition to 4-thio furanoid glycal: A highly stereoselective entry to 2'-deoxy-44'-thio pyrimidine nucleosides

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3713-3716

  Haraguchi, Kazuhiro ^a   Nishikawa, Ayako ^a   Sasakura, Eiko ^a   Tanaka, Hiromichi ^a   Nakamura, Kazuo T ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

Addition reactions; Glycals; Nucleosides; Thiosugars

Indexed keywords

FURAN DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032575191     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00543-7     Document Type: Article

References (26)

1. 1) (a) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782-2786,
2. (b) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Chem. Soc., Chem. Commun. 1991, 741-743.
3. (c) Secrist III, J. A.; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem, 1991, 34, 2361-2366.
4. (d) Uenishi, J.; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. J. Chem Soc., Chem. Commun. 1991, 1421-1422.
5. (e) Bellon, L.; Barascut, J.-I.; Imbach, J.-L. Nucleosides Nucleotides 1992, 11, 1467-1479.
6. (f) Huang, B.; Hui Y. Nucleosides Nucleotides 1993, 12, 139-147.
7. (g) Uenishi, J.; Motoyama, M.; Takahashi, K. Tetrahedron Asymm. 1994, 5, 101-106.
8. (h) Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasakai, T. Nucleosides Nucleotides 1994, 13, 1347-1361.
9. (i) Tiwari, K. N.; Secrist III, J. A.; Montgomery, J. A. Nucleosides Nucleotides 1994, 13, 1819-1828.
10. (j) Leydier, C.; Bellon, L.; Barascut, J.-L.; Deydier, J.; Maury, G.; Pelicano, H.; El Alaoui, M. A.; Imbach, J.-L. Nucleosides Nucleotides 1994, 13, 2035-2050.
11. (k) Secrist III, J. A.; Parker, W. B.; Tiwari, K. N.; Messini, L.; Shaddix, S. C.; Rose, L. M.; Bennett, L. L. Jr; Montgomery, J. A. Nucleosides Nudeotides 1995, 14, 675-686.
12. (l)Yoshimura, Y.; Kitano, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1996, 61, 822-833.
13. (m) Selwood, D. L.; Carter, K.; Young, R. J.; Jandu, K. S. Bioorg. Med. Chem. Lett. 1996, 6, 991-994.
14. (n) Hancox, E. L.; Walker, R. T. Nucleosides Nucleotides 1996, 15, 135-148.
15. (o) Uenishi, J. J. Synth. Org. Chem., Japan 1997, 55, 186-195.
16. (p) Yoshimura, Y.; Kitano, K.; Yamada, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Matsuda, A. J. Org. Chem. 1997, 61, 3140-3152.
17. 2) (a) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234-1255.
18. (b) Vorbrüggen, H.; Hofle, G. Chem. Ber. 1981, 114, 1256-1268.
19. 3) For a review of synthetic chemistry of glycals:Collins, P. M.; Ferrier, R. J. Monosaccharides, Their Chemistry and Their Roles in Natural Products. Chichester, U. K: John Wiley & Sons, 1995; pp. 317-326.
20. 4) Díaz, Y.; El-Langhdach, A.; Castillón, S. Tetrahedron 1997, 53, 10921-10938.
21. 5) Dyson, M. R.; Coe, P. L.; Walker, R. T. Carbohydrate Res. 1991, 216, 237-248.
22. 6) The yields of the elimination step in Scheme 2 and O-silylation in Scheme 3 were not optimized.
23. 7) The atomic coordinates for 17β are available on request from the Cambridge Crystallographic Data Centre, University of Chemical Laboratory, Lensfield Road, Cambridge CB21EW, UK.
24. 8) Similar protecting group-controlled stereoselective reactions have been observed in electrophilic addition to 1′,2′-unsaturated uracil nucleosides. (a) Itoh, Y.; Haraguchi, K.; Tanaka, H.; Gen, E.; Miyasaka, T. J. Org. Chem. 1995, 60, 656-662.
25. (b) Itoh, Y.; Haraguchi, K.; Tanaka, H.; Matsumoto, K.; Nakamura, K. T.; Miyasaka, T. Tetrahedron Lett. 1995, 36, 3867-3870. These face-selective electrophilic additions controlled by the silyl protecting groups can be accounted for as follows. In the case of TBDMS-protected glycal 8, 3-O-TBDMS group shields the α-face of the double bond. On the other hand, in the case of cyclic silyl protected glycals such as 10 or 11, the shielding of the α-face weakened. These steric environments lead to preferential α-face attack of the electrophilic reagent to increase the ratio of β-anomer / α-anomer, in the reaction of 10 and 11. In particular, in the case of 11, one of the two t-butyl groups, which is located in β-axial configuration, inhibits the approach of the reagent to the β-face to afford β-nucleoside as the sole product.
26. 9) The overall yields of the 2′-deoxy-4′-thionucleosides by this method were comparable to or better than that of the methods previously reported.