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The Crystal Structure of 3-Epismilagenin Acetate and 23-Oxo-3-epismilagenin Acetate

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Abstract

The crystal structure together with unambiguous assignation of 1H and 13C NMR signals of 3-epismilagenin acetate 4 and 23-oxo-3-epismilagenin acetate 5 are described. Compound 4, crystallized as orthorhombic system a = 10.535(1) Å, b = 13.775 (1) Å, c = 18.347 (1) Å, α = β = γ = 90°; with space group P2 1 2 1 2 1 ; while compound 5 crystallized as a monoclinic system a = 10.380(1) Å, b = 7.327(1) Å, c = 17.881(1) Å, α = γ = 90°, β = 99.56(1)°, with a space group P2 1 . The presence a carbonyl group at C(23) in compound 5 produces a significant deviation from the chair conformation observed in compound 4. The effects of the side chain modifications on the puckering parameters derived from are discussed.

Graphical Abstract

The crystal structure, together with unambiguous assignation of 1H and 13C NMR signals of two epismilagenin acetates, is described.

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Acknowledgments

The authors thank to the Dirección General de Asuntos del Personal Académico (DGAPA-UNAM) for financial support via project IN204008-3 and to CONACyT for scholarship granted to Mariana Macías-Alonso. Thanks are due to Georgina Duarte Lisci (USAI-UNAM) for registering Mass spectra.

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Authors and Affiliations

  1. Facultad de Química, Edificio B, Universidad Nacional Autónoma de México, Av. Universidad 3000, Coyoacán, Mexico, DF, 04510, Mexico

    Mariana Macías-Alonso, Nuria Esturau-Escofet, Marcos Flores-Álamo, Martín A. Iglesias-Arteaga & Rafael Moreno-Esparza

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  1. Mariana Macías-Alonso
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  2. Nuria Esturau-Escofet
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  3. Marcos Flores-Álamo
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  4. Martín A. Iglesias-Arteaga
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Correspondence to Rafael Moreno-Esparza.

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Macías-Alonso, M., Esturau-Escofet, N., Flores-Álamo, M. et al. The Crystal Structure of 3-Epismilagenin Acetate and 23-Oxo-3-epismilagenin Acetate. J Chem Crystallogr 41, 1476–1482 (2011). https://doi.org/10.1007/s10870-011-0126-3

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  • DOI: https://doi.org/10.1007/s10870-011-0126-3

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