Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of 2-Amino-4,6-Di-O-Benzoyl-3-O-Benzyl-1,2-Dideoxy Mannojirimycin

  • Published : 1995.09.20
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Abstract

Diacetone-D-glucose was converted into 5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose. After removal of isopropylidene and benzoyl protecting groups, hydrogenation performed reduction of azide and subsequent cyclization by reductive amination to give 3-O-benzyl-1-deoxy nojirimycin in high yield. The second azide group was introduced on 2-carbon by selective substitution reaction, and reduction of azide to amino group gave titled compound.

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References

  1. Ann. Rev. Biochem. v.56 Elbein, A. D.
  2. Angew. Chem. Int. Ed. Engl. v.20 Truscheit, E.;Frommer, W.;Junge, B.;Muller, L.;Schmidt, D. D.;Wingender, W.
  3. Metabolism v.34 Dimitriadis, G. D.;Tessari, P.;Go, V. L. W.;Gerich, J. E.
  4. Cancer Res. v.46 Humphries, M. J.;Matsumoto, K.;White, S. L.;Olden, K.
  5. J. Proc. Natl. Acad. Sci., U.S.A. v.84 Walker, B. D.;Kowalski, M.;Goh, W. C.;Kozarsky, K.;Krieger, M.;Rosen, C.;Rohrscheinder, L.;Haseltine, W. A.;Sodroski
  6. Nature v.330 Gruters, R. A.;Neefjes, J. J.;Termette, M.;Goede, R. E.;Tulp, A.;Huisman, H.;Miedema, F.;Ploegh, H. L.
  7. Lancet. v.i Sunkara, P. S.;Taylor, D. L.;Kang, M. S.;Bowling, T. L.;Liu, P. S.;Tyms, A. S.;Sjoerdsama, A.
  8. Lif. Sci. v.39 Scofield, A. M.;Fellow, L. E.;Nash, R. J.;Fleet, G. W.
  9. Biochim. Biophys. Acta. v.825 Fuhrmann, U.;Bause, E.;Ploegh, H.
  10. Nature v.307 Fuhrmann, U.;Bause, E.;Legler, G.;Ploegh, H.
  11. Tetrahedron Lett. v.29 Kite, G. C.;Fellows, L. E.;Fleet, G. W. J.;Liu, P. S.;Scofield, A. M.;Smith, N. G.
  12. Eur. Pat. Appl. v.EP 481 De, C. G. A.;Getman, D. P.
  13. J. Chem. abstr. v.93 Stoltefuss
  14. J. Carbohydr. Chem. v.10 Kiso, M.;Kitagawa, M.;Ishida, H.;Hasegawa, J.
  15. Tetrahedron Asymmetry v.4 Adron, H.;Butters, T. D.;Platt, F. M.;Wormald, M. R.;Dwek, R. A.;Fleet, G. W. J.;Jacob, G. S.
  16. J. Chem. Soc., Chem. Commun. Kilonda, A.;Compernolle, F.;Toppet, S.;Hoornaert, G. J.
  17. Purification of Laboratory Chemicals(3rd Ed.) Perrin, D. D.;Armarego, W. L. F.
  18. Bull. Korean Chem. Soc. v.14 Shin, Y.;Nam Shin, J. E.
  19. J. Tetrahedron Lett. v.26 Fleet, G. W. J.;Nicholas, S. J.;Smith, P. W.;Evans, S. V.;Fellows, L. E.;Nash, R. J.
  20. Tetrahedron Lett. v.29 Fleet, G. W. J.;Ramsden, N. G.;Molyneux, R. J.;Jacob, G. S.