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Synthesis and Molecular Structure of 1α-Hydroxy-13-Isopropyl-7,10A-Dimethyl-4-Oxooctadecahydro-4B,12-Methanochryseno[1,12-BC]Furan-7-Carboxylic Acid and Methyl 1β-Acetoxy-13-Acetyl-7,10A-Dimethyl-4-Oxohexadecahydro-1H-4B,12-Ethenochrysene-7-Carboxylate

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Abstract

New oxy-functionalized derivatives are synthesized by ozone oxidation of 1β,13- epoxydihydroquinopimaric acid and methyl ether of 1β-hydroxydihydroquinopimaric acid. Their molecular and crystal structures are determined by the single crystal X-ray diffraction analysis. 1α-Hydroxy-13-isopropyl-7,10a-dimethyl-4-oxooctadecahydro-4b,12-methanochryseno[1,12-bc]furan-7-carboxylic acid (II) is represented by crystalline hydrate of the monoclinic crystal system with the P21 space group, a = 12.3886(6) Å, b = 6.9442(3) Å, c = 13.7037(6) Å, β = 93.290(2)°. The presence of water molecules leads to the formation of a 2D network of hydrogen bonds making molecular layers parallel to (a, b). Crystals of methyl 1β-acetoxy-13-acetyl-7,10a-dimethyl-4-oxohexadecahydro-1H-4b,12-ethenochrysene-7-carboxylate (IV) are orthorhombic, space group P212121, a = 8.3760(3) Å, b = 16.2470(5) Å, c = 18.5603(6) Å.

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The work performed within State Assignment No. 1021062311392-9-1.4.1.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Russia

    E. V. Tret’yakova

  2. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. V. Rybalova & D. N. Polovyanenko

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  1. E. V. Tret’yakova
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  2. T. V. Rybalova
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  3. D. N. Polovyanenko
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Correspondence to E. V. Tret’yakova.

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Russian Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 11, 118295.https://doi.org/10.26902/JSC_id118295

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Tret’yakova, E.V., Rybalova, T.V. & Polovyanenko, D.N. Synthesis and Molecular Structure of 1α-Hydroxy-13-Isopropyl-7,10A-Dimethyl-4-Oxooctadecahydro-4B,12-Methanochryseno[1,12-BC]Furan-7-Carboxylic Acid and Methyl 1β-Acetoxy-13-Acetyl-7,10A-Dimethyl-4-Oxohexadecahydro-1H-4B,12-Ethenochrysene-7-Carboxylate. J Struct Chem 64, 2130–2136 (2023). https://doi.org/10.1134/S0022476623110100

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  • DOI: https://doi.org/10.1134/S0022476623110100

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