DOI QR코드

DOI QR Code

Synthesis of 2-Amino-4,6-Di-O-Benzoyl-3-O-Benzyl-1,2-Dideoxy Mannojirimycin

  • 발행 : 1995.09.20

초록

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.

키워드

참고문헌

  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.