A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives

Tetrahedron Letters

Volumn 47, Issue 18, 2006, Pages 3081-3084

  Boucheron, Charlotte ^a   Compain, Philippe ^a   Martin, Olivier R ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYGALACTONOJIRIMYCIN; 1 DEOXYMANNONOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN; 1 DEOXYNOJIRIMYCIN DERIVATIVE; ALCOHOL; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; PROTECTION; STEREOCHEMISTRY; SWERN OXIDATION;

EID: 33645873582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.157     Document Type: Article

References (42)

1. In: Stütz A.E. (Ed). Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (1999), Wiley-VCH, New York
2. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645
3. Bols M., Lillelund V.H., Jensen H.H., and Liang X. Chem. Rev. 102 (2002) 515
4. Mitrakou A., Tountas N., Raptis A.E., Bauer R.J., Schulz H., and Raptis S.A. Diab. Med. 15 (1998) 657
5. Compain P., and Martin O.R. Bioorg. Med. Chem. 9 (2001) 3077
6. Compain P., and Martin O.R. Curr. Top. Med. Chem. 3 (2003) 541
7. Moriyama H., Tsukida T., Inoue Y., Kondo H., Yoshino K., and Nishimura S.-I. Bioorg. Med. Chem. Lett. 13 (2003) 2737
8. Moriyama H., Tsukida T., Inoue Y., Yokota K., Yoshino K., Kondo H., Miura N., and Nishimura S.-I. J. Med. Chem. 47 (2004) 1930
9. Lee R.E., Smith M.D., Pickering L., and Fleet G.W.J. Tetrahedron Lett. 39 (1999) 8689
10. Lee R.E., Smith M.D., Nash R.J., Griffiths R.C., McNeil M., Grewal R.K., Yan W., Besra G.S., Brennan P.J., and Fleet G.W.J. Tetrahedron Lett. 38 (1997) 6733
11. Schramm V.L., and Tyler P.C. Curr. Top. Med. Chem. 3 (2003) 525
12. Iminosugars: Recent Insights into their Bioactivity and Potential as Therapeutic Agents. In: Martin O.R., and Compain P. (Eds). Current Topics in Medicinal Chemistry Vol. 3, issue 5 (2003), Bentham, Hilversum, Netherlands
13. Ye X.-S., Sun F., Liu M., Li Q., Wang Y., Zhang G., Zhang L.-H., and Zhang X.-L. J. Med. Chem. 48 (2005) 3688
14. See, for example:. Greimel P., Spreitz J., Stütz A.E., and Wrodnigg T.M. Curr. Top. Med. Chem. 3 (2003) 513
15. Robina I., Moreno-Vargas A.J., Carmona A.T., and Vogel P. Curr. Drug. Metab. 5 (2004) 329
16. Durantel D., Branza-Nichita, Carrouée-Durantel S., Butters T.D., Dwek R.A., and Zitzmann N. J. Virol. 75 (2001) 8987 and references cited
17. Somsak L., Nagy V., Hadazy Z., Docsa T., and Gergely P. Curr. Pharm. Design 9 (2003) 1177
18. Butters T.D., Dwek R.A., and Platt F.M. Chem. Rev. 100 (2000) 4683
19. Butters T.D., Dwek R.A., and Platt F.M. Glycobiology 10 (2005) 43R
20. Van der Spoel A.C., Jeyakumar M., Butters T.D., Charlton H.M., Moore H.D., Dwek R.A., and Platt F.M. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 17173
21. Suganuma R., Walden C.M., Butters T.D., Platt F.M., Dwek R.A., Yanagimachi R., and Van der Spoel A.C. Biol. Reprod. 72 (2005) 805
22. For recent reviews on the synthesis of iminosugars, see:. Afarinkia K., and Bahar A. Tetrahedron: Asymmetry 16 (2005) 1239
23. Pearson M.S.M., Mathé-Allainmat M., Fargeas V., and Lebreton J. Eur. J. Org. Chem. (2005) 2159
24. Cipolla L., La Ferla B., and Nicotra F. Curr. Top. Med. Chem. 3 (2003) 485
25. Godin G., Compain P., Masson G., and Martin O.R. J. Org. Chem. 67 (2002) 6960
26. Boucheron C., Desvergnes V., Compain P., Martin O.R., Lavi A., Mackeen M., Wormald M.R., Dwek R.A., and Butters T.D. Tetrahedron: Asymmetry 16 (2005) 1747
27. Mehta A., Conyers B., Tyrrell D.L.J., Walters K.-A., Tipples G.A., Dwek R.A., and Block T.M. Antimicrob. Agents Chemother. 46 (2002) 4004
28. Pavlovic D., Neville D.C.A., Argaud O., Blumberg B., Dwek R.A., Fischer W., and Zitzmann N. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 6104
29. N2 reaction led to untractable mixtures of products. These results may be due to the nucleophilic character of the endocyclic amine, which causes side reactions.
30. Jourdant A., and Zhu J. Tetrahedron Lett. 41 (2000) 7033
31. Ciufolini M.A., Hermann C.W., Whitmire K.H., and Byrne N.E. J. Am. Chem. Soc. 111 (1989) 3473
32. Badorrey R., Cativila C., Díaz-de-Villegas M.D., and Gálvez J.A. Tetrahedron 58 (2002) 341
33. Shirude P.S., Kumar V.A., and Ganesh K.N. Tetrahedron 60 (2004) 9485
34. 4) and concentrated under reduced pressure. Purification on silica gel (petroleum ether/ethyl acetate 6/1) afforded the secondary alcohol 8 as a colourless oil (151 mg, 77%).
35. 4Si requires 584.4135).
36. 4 requires 290.2331).
37. For a discussion of the general preference for axial or equatorial hydride delivery to cyclohexanones, see:. Wu Y.-D., Tucker J.A., and Houk K.N. J. Am. Chem. Soc. 113 (1991) 5018 and references cited
38. Carey F.A., and Sundberg R.A. Advanced Organic Chemistry. Part A: Structure and Mechanisms. 4th ed. (2000), Springer, New York
39. Chang et al. have recently reported a systematic study concerning the stereoselective reduction of ketosugars (hexosuloses):. Chang C.-W.T., Hui Y., Elchert B. Tetrahedron Lett. 42 (2001) 7019 and references cited
40. See, for example:. Kondo Y., Kashimura N., and Onodera K. Agric. Biol. Chem. 38 (1974) 2553
41. 4 requires 560.3740).
42. 4 requires 290.2331).