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

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Title: Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate.
Authors: Tinajero-Delgado, Verónica1, Romero-Ávila, Margarita1, Flores-Álamo, Marcos1, Arteaga, Martín1 martin.iglesias@unam.mx
Source: Journal of Chemical Crystallography. Sep2014, Vol. 44 Issue 9, p487-492. 6p.
Subjects: Cholic acid, Nuclear magnetic resonance, Methylene group, Crystal structure, Chirality, Bile acids
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 2 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. [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]
Copyright of Journal of Chemical Crystallography is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
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  Data: Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate.
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  Data: <searchLink fieldCode="AR" term="%22Tinajero-Delgado%2C+Verónica%22">Tinajero-Delgado, Verónica</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Romero-Ávila%2C+Margarita%22">Romero-Ávila, Margarita</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Flores-Álamo%2C+Marcos%22">Flores-Álamo, Marcos</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Arteaga%2C+Martín%22">Arteaga, Martín</searchLink><relatesTo>1</relatesTo><i> martin.iglesias@unam.mx</i>
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  Data: <searchLink fieldCode="DE" term="%22Cholic+acid%22">Cholic acid</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance%22">Nuclear magnetic resonance</searchLink><br /><searchLink fieldCode="DE" term="%22Methylene+group%22">Methylene group</searchLink><br /><searchLink fieldCode="DE" term="%22Crystal+structure%22">Crystal structure</searchLink><br /><searchLink fieldCode="DE" term="%22Chirality%22">Chirality</searchLink><br /><searchLink fieldCode="DE" term="%22Bile+acids%22">Bile acids</searchLink>
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  Data: 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 2 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. [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
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  Data: <i>Copyright of Journal of Chemical Crystallography is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1007/s10870-014-0543-1
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      – Code: eng
        Text: English
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      – SubjectFull: Cholic acid
        Type: general
      – SubjectFull: Nuclear magnetic resonance
        Type: general
      – SubjectFull: Methylene group
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      – SubjectFull: Crystal structure
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      – SubjectFull: Chirality
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      – SubjectFull: Bile acids
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      – TitleFull: Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate.
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              M: 09
              Text: Sep2014
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