Short efficient synthesis of the α-L-fucosidase inhibitor, deoxyfuconojirimycin [1,5-dideoxy-1,5-imino-l-fucitol] from d-lyxonolactone

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 3, 1989, Pages 665-666

  Fleet, George W J ^a   Petursson, Sigthor ^a,b   Campbell, Arthur L ^c   Mueller, Richard A ^c   Behling, James R ^c   Babiak, Kevin A ^c   Ng, John S ^c   Scaros, Mike G ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Biochemistry Department   (United Kingdom)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049089973     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19890000665     Document Type: Article

References (18)

1. G. W. J. Fleet, A. N. Shaw, S. V. Evans, and L. E. Fellows, J. Chem. Soc., Chem. Commun., 1985, 841.
2. R. Nuck, D. Sauvageot, H. Paulsen, R. Tauber, and W. Reutter, ‘Proceedings of the 9th International Symposium on Glycoconjugates,’ E37, Lille, France, 6–11 July, 1987; this communication proposes the name deoxyfuconojirimycin for (1).
3. G. W. J. Fleet, N. G. Ramsden, R. A. Dwek, T. W. Rademacher, L. E. Fellows, R. J. Nash, D. C. Green, and B. Winchester, J. Chem. Soc., Chem. Commun., 1988, 483.
4. A. Karpas, G. W. J. Fleet, R. A. Dwek, S. Petursson, S. K. Namgoong, N. G. Ramsden, G. S. Jacob, and T. W. Rademacher, Proc. Natl. Acad. Sci. USA, 1988, 85, 9229.
5. G. W. J. Fleet, A. Karpas, R. A. Dwek, L. E. Fellows, A. S. Tyms, S. Petursson, S. K. Namgoong, N. G. Ramsden, P. W. Smith, J. C. Son, F. X. Wilson, D. R. Witty, G. S. Jacob, and T. W. Rademacher, FEBS Lett., 1988, 237, 128.
6. H. S. Isbell, J. Res. Natl. Bur. Stand., 1942, 29, 227.
7. A. Thompson and M. L. Wolfrom, J. Am. Chem. Soc., 1946, 68, 1509.
8. W. J. Humphlett, Carbohydr. Res., 1967, 4, 157.
9. R. J. Schaffer, J. Res. Natl. Bur. Stand., Sect. A., 1961, 65, 507.
10. S. Morgenlie, Acta Chem. Scand. B., 1975, 29, 367.
11. Satisfactory spectral and microanalytical data were obtained for all new compounds reported in this paper.
12. Addition of alkyl-lithiums to sugar lactones to produce monoadducts is a well established procedure; see H. Ogura and H. Takahashi, J. Org. Chem., 1974, 39, 1374, and references therein.
13. H. Ogura, K. Furuhata, H. Takahashi, and Y. Iitaka, Chem. Pharm. Bull., 1978, 26, 2782.
14. G. W. J. Fleet, N. G. Ramsden, and D. R. Witty, Tetrahedron Lett., 1988, 29, 2871.
15. G. W. J. Fleet, N. G. Ramsden, and D. R. Witty, Tetrahedron., 1989, 45, 319.
16. T. K. M. Shing, J. Chem. Soc., Chem. Commun., 1988, 1221.
17. Assistance from K. T. McLaughlin, Owen Goodmonson, Michael L. Prunier, and Pat Finnegan of G. D. Searle Research and Development is gratefully acknowledged.
18. An alternative synthesis of compound (1) from 2-azidogalactose has been reported: H. Paulsen and M. Maatske, Liebigs Ann. Chem., 1988, in press.