Skip to main content
SpringerLink
Log in

Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The crystal structure and NMR characterization of methyl 3α,7α-dihydroxy-12-oxo-5β-cholanate are described. The title compound which was obtained from methyl cholanate in a 3-step synthetic sequence that does not alter the starting chirality, crystallizes in the monoclinic system with P 21 space group. While despite the substitution pattern rings A, B and C adopt chair conformations, the 5 membered D ring, that bears the side chain attached to C-17, shows a twisted conformation on C-13–C-14. In the crystal array, classical hydrogen bond interactions O–H···H and intermolecular contacts C–H···O of hydrogen bond type are observed.

Graphical Abstract

The crystal structure and NMR characterization of Methyl α,7α-dihydroxy-12-oxo-5β-cholanate are described.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Fieser L, Feiser M (1959) Steroids. Reinhold, New York and references therein

    Google Scholar 

  2. Setchell KDR, Kritchevsky D, Nair PP (1971) The bile acids, vol 1. Plenum, New York, pp 1–25 249–283

    Google Scholar 

  3. Montse MJ, Marin JGC, Antelo A, Vázquez-Tato J (2009) World J Gastroenterol 21(15):804–816

    Article  Google Scholar 

  4. Lemos TLG, McChesney JD (1990) J Nat Prod 53:152–156

    Article  CAS  Google Scholar 

  5. Hirschmann R (1992) Steroids 57(12):579–592

    Article  CAS  Google Scholar 

  6. Zhou W-S, Huang L-F (1992) Tetrahedron 48:1837–1852

    Article  CAS  Google Scholar 

  7. Perez-Gil R, Iglesias-Arteaga MA, Perez-Martinez C, Coll-Manchado F, Coll-Garcia D, Rosado A (1998) Eur J Org Chem 2405–2407

  8. Dias JR, Nassim B (1980) Steroids 35:405–417

    Article  CAS  Google Scholar 

  9. Jurček O, Wimmer Z, Svobodová H, Bennettová B, Kolehmainen K, Drašar P (2009) Steroids 74:779–785

    Article  Google Scholar 

  10. Tamminen J, Kolehmainen E (2001) Molecules 6:21–46

    Article  CAS  Google Scholar 

  11. Fieser LF, Rajagopalan S (1950) J Am Chem Soc 72:5530–5536

    Article  CAS  Google Scholar 

  12. Chang F (1979) J Org Chem 44(25):4567–4572

    Article  CAS  Google Scholar 

  13. Oxford Diffraction (2009) CrysAlis CCD and CrysAlis Red. Oxford Diffraction, Abingdon

    Google Scholar 

  14. Clark RC, Reid JS (1995) Acta Cryst A51:887–897

    Article  CAS  Google Scholar 

  15. Sheldrick GM (2008) Acta Cryst A64:112–122

    Article  Google Scholar 

  16. Farrugia LJ (1997) J Appl Crystallogr 30:565

    Article  CAS  Google Scholar 

  17. Farrugia LJ (1999) J Appl Crystallogr 32:837–838

    Article  CAS  Google Scholar 

  18. Flack HD (1983) Acta Cryst A 39:876–881

    Article  Google Scholar 

  19. Hooft RWW, Straver LH, Spek AL (2008) J Appl Crystallogr 41:96–103

    Article  CAS  Google Scholar 

  20. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354–1358

    Article  CAS  Google Scholar 

  21. Duax WL, Weeks CM (1976) Rohrer DC. In: Eliel EL, Allinger N (eds) Topics in stereochemistry, vol 2. Wiley, New York, pp 271–283

    Chapter  Google Scholar 

  22. Altona C, Geise HJ, Romers C (1968) Tetrahedron 24:13–32

    Article  CAS  Google Scholar 

  23. Etter MC (1990) MacDonald JC. Acta Cryst B 46:256–262

    Article  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the financial support provided by Dirección General de Asuntos del Personal Académico (Project DGAPA-IN211714) and the Faculty of Chemistry (PAPIIT-5000-9063). Thanks are due to Rosa I. del Villar Morales (USAI-UNAM) for recording NMR spectra and to Dr. Carlos Cobas from Mestrelab® for assistance with the MestreNova NMR processing program.

Author information

Authors and Affiliations

  1. Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Mexico, D.F., Mexico

    Verónica Tinajero-Delgado, Margarita Romero-Ávila, Marcos Flores-Álamo & Martín A. Iglesias Arteaga

Authors
  1. Verónica Tinajero-Delgado
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Margarita Romero-Ávila
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marcos Flores-Álamo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Martín A. Iglesias Arteaga
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Martín A. Iglesias Arteaga.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tinajero-Delgado, V., Romero-Ávila, M., Flores-Álamo, M. et al. Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate. J Chem Crystallogr 44, 487–492 (2014). https://doi.org/10.1007/s10870-014-0543-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-014-0543-1

Keywords

Search

Navigation