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(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol.

ABSTRACT: The title steroidal compound, C(29)H(47)NO(4), was prepared in a one-pot reaction starting from a sarsasapogenin derivative of known configuration. The isoxazole heterocycle is oriented towards the α face of the steroid nucleus and, although fully functionalized on C atoms, does not provoke steric hindrance with the adjacent D ring. The absolute configuration observed for chiral centers is as expected, and shows that no epimerization occurred in the precursors. In the crystal, the three OH groups serve as donors for hydrogen bonding with O and N atoms. The isoxazole N atom is involved in O-H⋯N hydrogen bonds, forming chains along [100]. These chains are further connected via O-H⋯O and weak C-H⋯O contacts, giving rise to a three-dimensional supra-molecular network.

SUBMITTER: Hernandez Linares MG

PROVIDER: S-EPMC2972099 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate.

Project description:THE STRUCTURE OF THE TITLE STEROID [ALTERNATIVE NAME: 3β,6β-diacet-oxy-5β-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5α-ol derivative reported a century ago by Westphalen. The methyl group at position 10 of the starting material migrates to position 5 in the steroidal nucleus, while a Δ(9) bond is formed, as indicated by the C=C bond length of 1.347 (4) Å. The methyl transposition leaves the 5R configuration unchanged, with the methyl oriented towards the β face. During the rearrangement, the steroidal B ring experiences a conformational distortion from chair to envelope with the C atom at position 6 as the flap. In the title structure, the isopropyl group of the side chain is disordered over two positions, with occupancies of 0.733 (10) and 0.267 (10). The carbonyl O atom in the acetyl group at C3 is also disordered with an occupancy ratio of 0.62 (4):0.38 (4).

| S-EPMC3588934 | biostudies-literature

6β-Acetamido-5α-hydroxy-cholestan-3β-yl acetate.

Project description:The title steroid, C(31)H(53)NO(4), was prepared from the corresponding 5α,6α-epoxy-cholestane. The conformation of the six-membered rings is close to a chair form, while the five-membered ring adopts a twist conformation. The hydroxyl and acetamide groups are in axial positions. The nucleophilic species bound to the steroid nucleus at position 6 by the β-face, whereas the hydroxyl group at position 5 has α-orientation. All rings are trans-fused. The crystal packing shows that the mol-ecules related by twofold symmetry exist as O-H⋯O hydrogen-bonded dimers.

| S-EPMC2959794 | biostudies-literature

The zwitterion (23'E)-(23R,25S)-23-[1-(oxidoiminio)eth-yl]-5β-spiro-stan-3β-yl acetate.

Project description:The title steroidal compound, C(31)H(49)NO(5), resulted from the selective oximation of (23R)-23-acetyl-sarsasapogenin acetate. One- and two-dimensional (1)H and (13)C NMR spectra, as well as IR data, are in agreement with the presence of a ketoxime group at C-23. However, recrystallization in slightly acidic media affords the title compound in the rare zwitterionic oxime form, as a consequence of migration of the hydr-oxy H atom to the N atom in the oxime group. This H atom is clearly detected and its position was refined from X-ray data. The geometry for the C=N(+)(H)-O(-) group features long C=N and short N-O bond lengths compared to non-zwitterionic oximes. The ketoxime is stabilized with the E configuration, avoiding steric hindrance between the oxime O atom and H atom at C-23. The sum of the angles around the oxime N atom is 359.6°, giving a planar configuration for that atom, as expected for sp(2) hybridization.

| S-EPMC2970983 | biostudies-literature

(20S)-Dammar-24-ene-3?,20-diol monohydrate from the bark of Aglaia exima (Meliaceae).

Project description:In the title compound {systematic name: (1R,2R,5R,7R,10R,11R,14S,15R)-14-[(2S)-2-hy-droxy-6-methyl-hept-5-en-2-yl]-2,6,6,10,11-penta-methyl-tetra-cyclo-[8.7.0.0(2,7).0(11,15)]hepta-decan-5-ol monohydrate}, C(30)H(52)O(2)·H(2)O, the three fused cyclo-hexane rings adopt chair conformations and the hy-droxy substituent of one of these occupies an axial position. The fused cyclo-pentane ring adopts an envelope conformation (with the flap atom being the C atom bearing the methyl group) and the 3-methyl-but-2-enyl portion of its substituent is disordered over three sets of sites in a 0.413?(7):0.250?(7):0.337?(7) ratio. The O atoms of both water mol-ecules occupy special positions of 2 site symmetry. In the crystal, O(s)-H?O(w) and O(w)-H?O(s) (s = steroid and w = water) hydrogen bonds link hy-droxy groups and water mol-ecules, forming a three-dimensional network. The crystal studied was found to be a non-merohedral twin with a 0.518?(1):0.482?(1) component ratio.

| S-EPMC3435729 | biostudies-literature

Cholest-5-en-3β-yl 3-(4-eth-oxy-phen-yl)prop-2-enoate.

Project description:In the asymmetric unit of the title compound, C(38)H(56)O(3), there are two symmetry-independent mol-ecules that differ in the rotation angle along the C-O bond between the 3-(4-eth-oxy-phen-yl)prop-2-enoate and cholest-5-en-3β-yl groups by 169.3 (3)°. In both mol-ecules, steroid ring B adopts a half-chair conformation, rings A and C adopt a chair conformation and ring D exists in an envelope form. The two symmetry-independent mol-ecules pack in the crystal into separate layers parallel to (-102) with their long axis parallel to the [201] direction. Short inter-molecular C-H⋯O and C-H⋯π contacts are observed.

| S-EPMC3393328 | biostudies-literature

6β-Chloro-5α-hydr-oxy-20-oxopregnan-3β-yl acetate.

Project description:The title steroid, C(23)H(35)ClO(4), is a pregnane derivative prepared by ring opening of the corresponding 5α,6α-ep-oxy steroid with BiCl(3). There are two symmetry-independent mol-ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings in both mol-ecules is close to a chair form, while the five-membered ring adopts an envelope conformation. All rings in both mol-ecules are trans-fused. The mol-ecules are held together by an extensive O-H⋯O hydrogen-bonding network.

| S-EPMC2962054 | biostudies-literature

1-[4-(3-Chloro-prop-oxy)-2-hydroxy-phen-yl]ethanone.

Project description:The title compound, C(11)H(13)ClO(3), has been obtained in the reaction of 2, 4-dihydroxy-lacetonephenone, potassium carbonate and 1-bromo-3-chloro-hexane. The hydr-oxy group is involved in an intra-molecular O-H?O hydrogen bond. The crystal packing exhibits no significantly short inter-molecular contacts.

| S-EPMC2980010 | biostudies-literature

(1S,2R,4S)-1-[(Benzyl-amino)-meth-yl]-4-(prop-1-en-2-yl)cyclo-hexane-1,2-diol.

Project description:The title compound, C(17)H(25)NO(2), was synthesized by epoxidation of the double bond of (S)-perillyl alcohol [(S)-4-isopropenyl-1-cyclo-hexenyl-methanol], followed by the oxirane ring-opening by benzyl-amine using [Ca(CF(3)CO(2))(2)] as catalyst under solvent-free condition at 313?K. The mol-ecular conformation is stabilized by an intra-molecular O-H?N hydrogen bond. In the crystal, mol-ecules are linked by inter-molecular N-H?O hydrogen bonds, forming chains parallel to the a axis, which are further connected by O-H?O hydrogen bonds into sheets parallel to (010). The absolute configuration of the mol-ecule is known from the synthetic procedure.

| S-EPMC3050382 | biostudies-literature

(20S)-20-Acetamido-18-chloro-5?-pregnan-3?-yl acetate.

Project description:In the title compound, C(25)H(40)ClNO(3), prepared by the thermolysis of (20S)-O,N-diacetyl-20-amino-N-chloro-3?-hydr-oxy-5?-pregnane, the three six-membered rings adopt chair conformations while the five-membered ring is in an envelope conformation. The ester group attached to ring A is in an equatorial position. All the rings are trans-fused. Intra-molecular C-H?O and C-H?Cl inter-actions occur. The crystal structure is stabilized by inter-molecular N-H?O and C-H?O inter-actions close contacts occur.

| S-EPMC2983833 | biostudies-other

(E)-3-(4-Hexyl-oxyphen-yl)-1-(3-hydroxy-phen-yl)prop-2-en-one.

Project description:In the title compound, C(21)H(24)O(3), the enone unit is in the s-cis configuration. The dihedral angle between the benzene rings is 2.18 (4)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O inter-molecular hydrogen bonds, forming inversion dimers. The crystal structure is also consolidated by C-H⋯π inter-actions.

| S-EPMC2968884 | biostudies-literature

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