3β,6β-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate

The title compound, C31H48O7, a polyoxygenated steroid, was obtained by chemical oxidation of 7-dehydrocholesteryl acetate. The molecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intramolecular S(6) O—H⋯O hydrogen-bonding motif involving a hydroxy donor and acceptor is observed. In the crystal, chains of molecules running along the b axis are formed via O—H⋯O hydrogen bonds between hydroxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 21 screw axes.

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3β,6α-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one

Piccialli

Tuzi

Oliviero

et al. 2013

Acta Cryst E

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(3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

et al. 2013

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(3S,3aS,6R,6aR)-2-Oxohexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

et al. 2013

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The title compound, C20H16O7, contains a cis-fused γ-lactone tetrahydrofuran ring system functionalized with two benzoyloxy groups. Both rings adopt an envelope conformation. The molecule assumes an elongated shape and exibits non-crystallographic C 2 symmetry. The benzoyloxy groups are almost planar [maximum deviations of 0.0491 (15) and 0.0336 (17) Å for the O atoms] and their mean planes are inclined to one another by 16.51 (4)°. The crystal packing features weak C—H⋯O interactions. The aryl groups of adjacent molecules are parallel shifted with face-to-face contacts and a shortest intermolecular C⋯C distance of 3.482 (4) Å.

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3β,6β-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one acetic acid 0.04-solvate

Cited by 3 publications

References 26 publications

3β,6α-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one

3β,6α-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one

(3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

(3S,3aS,6R,6aR)-2-Oxohexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

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