Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Stereospecific Synthesis of (+)-2-Epideoxymannojirimycin and (2R,3R,4R,5R)-3,4,5-Trihydroxypipecolic Acid

  • Published : 1995.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

2-Epideoxymannojirimycin 1 and (2R,3R,4R,5R)-3,4,5-trihydroxypipecolic acid 2 were prepared starting from D-glucosamic acid as a chiral educt. Key transformations were selective removal of the terminal isopropylidene group and intramolecular cyclization by SN2 reaction.

Keywords

References

  1. Biochemistry v.24 Dale, M. P.;Ensely, H. E.;Kern, K.;Sastry, K. A. R.;Byers, L. D.
  2. Biochem. J. v.258 Al Daher, S.;Fleet, G.;Namgoong, S. K.;Winchester, B.
  3. J. Chem. Soc., Chem. Commun. Fellows, L. E.;Bell, E. A.;Lynn, D. G.;Pilkiewcz, F.;Miura, I.;Nakanishi, K.
  4. Nature v.307 Fuhrmann, U.;Bause, E.;Legler, G.;Ploegh, H.
  5. Arch. Biochem. Biophs. v.235 Elbein, A. D.;Legler, G.;Tlusty, A.;McDowell, W.;Schwarz, R.
  6. J. Chem. Soc., Chem. Commun. Manning, K. S.;Lynn, D. G.;Shabanowitz, J.;Fellows, L. E.;Singh, M.;Schrire, B. D.
  7. FEBS Lett. v.176 di BelloI, C.;Dorling, P.;Fellow, L. E.;Winchester, B.
  8. Terahedron Lett. v.25 Fleet, G. W. J.;Gough, M. J.;Shing, T. K. M.
  9. Tetrahedron Lett. v.26 Bernotas, R. C.;Ganem, B.
  10. Tetrahedron lett. v.29 Pederson, R. L.;Kim M.-J.;Wong, C. -H.
  11. Tetrahedron Lett. v.29 Fleet, G. W. J.;Ramsden, N. G.;Witty, D. R.
  12. J. Chem. Soc., Chem. Soc., Chem. Commun. v.854 Dondoni, A.;Fantin, G.;Fogagnolo, M.;Merino, P.
  13. Carbohydr. Res. v.242 Izquierdo Cubero, I.;Lopez-Espinosa, M. T. P.;Richardson, A. C.;Suarez Ortega, M. D.
  14. Tetrahedron Lett. v.43 Fleet, G. W. J.;Fellows, L. E.;J. C. Son.
  15. Synthesis v.201 Brook, M. A.;Chan, T. H.
  16. Tetrahedron Lett. v.35 Park, K. H.;Yoon, Y. J.;Lee, S. G.