A selective ring opening reaction of 4,6-O-benzylidene acetals in carbohydrates using trialkylsilane derivatives

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5547-5551

  Sakagami, Masahiro ^a   Hamana, Hiroshi ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4,6 BENZYLIDENEGLUCOSE; ACETAL DERIVATIVE; ASPARAGINE LINKED OLIGOSACCHARIDE; CARBOHYDRATE; ETHER DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; QUANTITATIVE ASSAY; REDUCTION; STEREOCHEMISTRY;

EID: 0034661876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00877-7     Document Type: Article

References (26)

1. (a) Ashwell, G.; Harford, J. Annu. Rev. Biochem. 1982, 51, 531-554
2. (b) Suzuki, Y. Virology 1992, 189, 121-131.
3. (c) Imai, Y.; Lasky, L. A.; Rosen, S. D. Nature 1993, 361, 555-557.
4. (d) Perillo, N. L.; Pace, K. E.; Seihamer, J. J.; Baum, L. G. Nature 1995, 378, 736-739.
5. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130-1132.
6. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Bevilacqua, M.; Seed, B. Science 1990, 250, 1132-1135.
7. (c) Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196-197.
8. (d) Bevilacqua, M.; Pober, J. S.; Mendrick, D. L.; Cotran, R. S.; Gimbrone Jr., M. A. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 9238-9242.
9. (e) Bevilacqua, M.; Stengelin, S.; Gimbrone Jr., M. A.; Seed, B. Science 1989, 243, 1160-1165.
10. (f) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, R. M. Cell 1990, 63, 475-484.
11. (a) Sakagami, M.; Horie, K.; Nakamoto, K.; Kawaguchi, K.; Hamana, H. Bioorg. Med. Chem. Lett. 1998, 8, 2783-2786.
12. (b) Horie, K.; Sakagami, M.; Kuramochi, K.; Hanasaki, K.; Hamana, H. Pharm. Res. 1999, 16, 314-320.
13. Garegg, J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
14. Deninno, M.P.; Etienne, J.B.; Duplantier, K.C. Tetrahedron Lett. 1995, 36, 669-672.
15. (a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. Int. Ed. 1996, 35, 1380-1419.
16. (b) Holst, O. Angew. Chem., Int. Ed. 1995, 34, 2000-2002.
17. Sanders, W. J.; Manning, D. D.; Koeller, K. M.; Kiessling, L. L. Tetrahedron 1997, 53, 16391-16422.
18. Molecular sieves were dried at 140°C over 4 h with vacuation (ca. 0.1 mmHg).
19. Guindon, Y.; Girard, Y.; Berthiaume, S.; Gorys, V.; Lemieux, R.; Yoakim, C. Can. J. Chem. 1990, 68, 897-902.
20. (a) Jiang, L.; Chan, T.-K. Tetrahedron Lett. 1998, 39, 355-358.
21. (b) Okawa, M.; Liu, W. C.; Nakai, Y.; Koshida, S.; Fukase, K.; Kusumoto, S. Synlett 1996, 1179-1180.
22. We reported that allyltrimethylsilane reacted with various nitriles in the presence of boron trichloride. Hamana, H.; Sugasawa, T. Chem. Lett. 1985, 921-924.
23. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
24. (b) Hermkens, P. H. H.; Ottenheijim, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678.
25. TM (0.81 mmol/g) was purchased from Argonaut Technologies Inc. Hu, Y.; Porco, J. A.; Labadie, J. W.; Gooding, O. W.; Trost, B. M. J. Org. Chem. 1998, 63, 4518-4521.
26. 3:MeOH=100:1) giving 2 (262 mg, 87%).