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Ethyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate

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Abstract

The crystal structure, at 120 K, and solution 1H and 13C NMR spectra of ethyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate, (8) have been determined. Compound 8 crystallizes in the triclinic space group, P1 (Z = 1) with a = 6.0209(3) Å, b = 8.9698(5) Å, c = 9.9818(8) Å, α = 104.965(2)°, β = 98.522(3)°, γ = 106.790(5)°. The Cremer and Pople puckering parameters [Q = 0.602(4) Å, θ = 7.1(4)°, φ = 325(3)°] for the pyranose ring in the solid state indicate a near ideal 4C1 chair conformation with a slight distortion in the direction towards 0H5. A number of weak, soft intermolecular C–H ⋅ ⋅ ⋅ O hydrogen bonds set up a 3D array. NMR spectra and FAB and EIMS data have been obtained. Solution NMR parameters suggest that the solid state conformation is maintained in solution in chloroform.

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References

  1. Spahn-Langguth, H.; Benet, L.Z. Drug Metab. Rev. 1992, 24, 5

    Google Scholar 

  2. Brimacombe, J.S.; Webster, J.M. Mucopolysaccharides; Elsevier: Amsterdam, 1964.

    Google Scholar 

  3. Allen, F.H.; Kennard, O. Chem. Des. Autom. News 1993, 1and 31.

  4. Fletcher, D.A.; McMeeking, R.F.; Parkin, D. J. Chem. Inf. Comput. Sci. 1997, 36, 746.

    Google Scholar 

  5. DeLucas, L.J.; Gartland, G.L.; Bugg, C.E. Carbohydr. Res. 1978, 62, 213.

    Google Scholar 

  6. Gurr, G.E. Acta Crystallogr. 1963, 16, 690.

    Google Scholar 

  7. DeLucas, L.J.; Bugg, C.E.; Terzis, A.; Rivest, R. Carbohydr. Res. 1975, 41, 19.

    Google Scholar 

  8. Flippen, J.L.; Gilardi, R.D. Acta Crystallogr., Sect. B 1974, 30, 537.

    Google Scholar 

  9. Perrier, P.R.; Bryn, S.R. J. Org. Chem. 1982, 47, 4677.

    Google Scholar 

  10. Trynda, A.; Madaj, J.; Konitz, A.; Wisniewski, A. Carbohydr. Res. 2000, 329, 249.

    Google Scholar 

  11. Doherty, R.M.; Stewart, J.M.; Benson, W.R.; Maienthal, M.M.; DeCamp, W.H. Carbohydr. Res. 1983, 116, 150.

    Google Scholar 

  12. Antel, J.; Sheldrick, G. M.; Leiting, B.; Tietze, L.-T. Acta Crystallogr., Sect. C 1989, 45, 60.

    Google Scholar 

  13. Desiraju, G.R. Acc. Chem. Res. 1991, 24, 290

    Google Scholar 

  14. Desiraju, G.R. Acc. Chem. Res. 1996, 29, 441

    Google Scholar 

  15. Steiner, T. Chem. Commun. 1997, 727

  16. Steiner, T.; Desiraju, G. R. Chem. Commun. 1998, 891.

  17. Glidewell, C.; Harrison, W.T.A.; Low, J.N.; Sime, J.G.; Wardell, J.L. Acta Crystallogr., Sect. B 2001, 57, 190.

    Google Scholar 

  18. Tsukamoto, H.; Hamana, M.; Kato, K.; Kurada, T. J. Pharm. Soc., Jpn. 1956, 76, 1282.

    Google Scholar 

  19. Imamura, T.; Watanabe, T.; Kuwahara, M.; Koshijima, T. Phytochemistry. 1994, 37, 1165.

    Google Scholar 

  20. Sheldrick, G.M. Acta Crystallogr., Sect. A 1990, 46, 467.

    Google Scholar 

  21. Sheldrick, G.M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.

    Google Scholar 

  22. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.

    Google Scholar 

  23. Hooft, R. COLLECT; Nonius: Delft, The Netherlands, 1998.

    Google Scholar 

  24. Blessing, R.H. Acta Crystallogr., Sect. A 1995, 51, 33

    Google Scholar 

  25. Blessing, R.H. J. Appl. Crystallogr. 1997, 30, 421.

    Google Scholar 

  26. Farrugia, L.J. J. Appl. Crystallogr. 1997, 30, 565.

    Google Scholar 

  27. Spek, A.L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2000.

    Google Scholar 

  28. McArdle, P. J. Appl. Crystallogr. 1994, 27, 438.

    Google Scholar 

  29. Cremer, D.; Pople, J.A. J. Am. Chem. Soc. 1975, 97, 1354.

    Google Scholar 

  30. Koll, P.; Saak, W.; Pohl, S.; Steiner, B.; Koós, M. Carbohydr. Res. 1994, 265, 237.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland

    Thomas C. Baddeley, Janet M.S. Skakle & James L. Wardell

  2. Quadrant Healthcare Ltd., 1 Mere Way, Ruddington, Nottingham, NG11 6JS, England

    Iain G. Davidson

Authors
  1. Thomas C. Baddeley
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  2. Iain G. Davidson
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  3. Janet M.S. Skakle
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  4. James L. Wardell
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Correspondence to Janet M.S. Skakle.

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Baddeley, T.C., Davidson, I.G., Skakle, J.M. et al. Ethyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate. Journal of Chemical Crystallography 33, 33–38 (2003). https://doi.org/10.1023/A:1021347732701

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