Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

(3S,5R,6S)-Di-phenyl-methyl 1-oxo-6-bromo-penicillanate.

ABSTRACT: In the title compound, C₂₁H₂₀BrNO₄S, a key inter-mediate in the synthesis of the widely used β-lactamase inhibitor tazobactam, the five-membered thia-zolidine ring adopts an envelope conformation and the four-membered azetidine ring is in a distorted planar conformation. The crystal structure features C-H⋯O hydrogen bonds and a weak C-H⋯π inter-action.

SUBMITTER: Soundararajan K

PROVIDER: S-EPMC9462188 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

(3S,5R,6S)-Di-phenyl-methyl 1-oxo-6-bromo-penicillanate.

Soundararajan Krishnan K Sethuraman Velusamy V Thanigaimani Kaliyaperumal K

IUCrData 20200211 Pt 2

In the title compound, C21H20BrNO4S, a key inter-mediate in the synthesis of the widely used β-lactamase inhibitor tazobactam, the five-membered thia-zolidine ring adopts an envelope conformation and the four-membered azetidine ring is in a distorted planar conformation. The crystal structure features C-H⋯O hydrogen bonds and a weak C-H⋯π inter-action. ...[more]

PMID: 36340841

Similar Datasets

(1R,3S,5R,6S)-6-Hydr-oxy-3-tosyl-oxy-tropan-8-ium chloride.

Project description:The title compound, C(15)H(22)NO(4)S(+)·Cl(-), is a hydrolysis product of lesatropane [(1R,3S,5R,6S)-6-acet-oxy-3-tosyl-oxytropane] hydro-chloride, a potential anti-glaucoma agent. As in lesatropane, the piperidine and pyrrolidine rings in the title compound adopt chair and envelope conformations, respectively. There are two mol-ecules in the unit cell with similar conformations. The crystal structure is stabilized by inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds.

| S-EPMC2979886 | biostudies-literature

(1R,3S,5R,6S)-6-Acet-oxy-3-(4-methyl-phenyl-sulfon-yloxy)tropane.

Project description:IN THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,3S,5R,6S)-8-methyl-3-(4-methyl-phenyl-sulfon-yloxy)-8-aza-bicyclo-[3.2.1]octan-6-yl acetate], C(17)H(23)NO(5)S, the fused piperidine ring exists in a chair conformation with the N atom and one C atom displaced by 0.876 (2) and -0.460 (3) Å, respectively, on opposite sides of the mean plane defined by the other four atoms. The fused pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.644 (3) Å from the mean plane of the other four atoms.

| S-EPMC2960129 | biostudies-literature

Ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-3-{(3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-5-oxoisoxazolidin-2-yl}propanoate chloroform monosolvate

Project description:The Flack and Watkin 2AD plot based on 1941 acentric Friedel pairs for the title chloroform solvate shows that the observed intensity differences for Friedel opposites are dominated by random and systematic errors, erasing information about resonant scattering. The title compound, C22H33NO12·CHCl3, was obtained as a product of a double aza-Michael addition of hydroxylamine on a Chiron with a known absolute configuration. The enantiopure compound crystallized as a chloroform solvate, in space group P1, and diffraction data were collected at room temperature with Ag Kα radiation. The Flack parameter refined to x = −0.01 (16); however, the Flack and Watkin 2AD plot clearly shows that differences between Friedel opposites (the D component of the plot) do not carry any reliable information about resonant scattering of Cl atoms, and are rather dominated by random and systematic errors. The RD factor calculated using 1941 acentric Friedel pairs is RD = 0.995. On the other hand, the 2A component of the plot, related to average intensities of Friedel pairs, shows that data are of good quality (RA = 0.069). This example illustrates that while using Ag Kα radiation (λ = 0.56083 Å), scatterers heavier than Cl should be present in a chiral crystal in order to determine confidently the absolute structure of the crystal.

| S-EPMC9462232 | biostudies-literature

Interconversion of the cis-5R,6S- and trans-5R,6R-thymine glycol lesions in duplex DNA.

Project description:Thymine glycol (Tg), 5,6-dihydroxy-5,6-dihydrothymine, is formed in DNA by the reaction of thymine with reactive oxygen species. The 5R Tg lesion was incorporated site-specifically into 5'-d(G(1)T(2)G(3)C(4)G(5)Tg(6)G(7)T(8)T(9)T(10)G(11)T(12))-3'; Tg = 5R Tg. The Tg-modified oligodeoxynucleotide was annealed with either 5'-d(A(13)C(14)A(15)A(16)A(17)C(18)A(19)C(20)G(21)C(22)A(23)C(24))-3', forming the Tg(6) x A(19) base pair, corresponding to the oxidative damage of thymine in DNA, or 5'-d(A(13)C(14)A(15)A(16)A(17)C(18)G(19)C(20)G(21)C(22)A(23)C(24))-3', forming the mismatched Tg(6) x G(19) base pair, corresponding to the formation of Tg following oxidative damage and deamination of 5-methylcytosine in DNA. At 30 degrees C, the equilibrium ratio of cis-5R,6S:trans-5R,6R epimers was 7:3 for the duplex containing the Tg(6) x A (19) base pair. In contrast, for the duplex containing the Tg(6) x G(19) base pair, the cis-5R,6S:trans-5R,6R equilibrium favored the cis-5R,6S epimer; the level of the trans-5R,6R epimer remained below the level of detection by NMR. The data suggested that Tg disrupted hydrogen bonding interactions, either when placed opposite to A(19) or G(19). Thermodynamic measurements indicated a 13 degrees C reduction of T(m) regardless of whether Tg was placed opposite dG or dA in the complementary strand. Although both pairings increased the free energy of melting by 3 kcal/mol, the melting of the Tg x G pair was more enthalpically favored than was the melting of the Tg x A pair. The observation that the position of the equilibrium between the cis-5R,6S and trans-5R,6R thymine glycol epimers in duplex DNA was affected by the identity of the complementary base extends upon observations that this equilibrium modulates the base excision repair of Tg [Ocampo-Hafalla, M. T.; Altamirano, A.; Basu, A. K.; Chan, M. K.; Ocampo, J. E.; Cummings, A., Jr.; Boorstein, R. J.; Cunningham, R. P.; Teebor, G. W. DNA Repair (Amst) 2006, 5, 444-454].

| S-EPMC2646635 | biostudies-literature

(1R,3S,5R,6S)-6-Acet-oxy-8-methyl-3-(p-tolyl-sulfon-yloxy)-8-azoniabicyclo-[3.2.1]octane (2R,3R)-2,3-bis-(benzo-yloxy)-3-carboxy-propanoate.

Project description:The title compound, C(17)H(24)NO(5)S(+)·C(18)H(13)O(8) (-), is the key inter-mediate during the preparation of lesatropane [systematic name (1R,3S,5R,6S)-6-acetoxy-3-(4-methylphenylsulfonyloxy)tropane], a potential anti-glaucoma agent. The tertiary N atom of the tropane ring is involved in inter-molecular N-H⋯O hydrogen bonding, and the carboxylate groups are involved in inter-molecular O-H⋯O hydrogen bonding.

| S-EPMC2977720 | biostudies-literature

(4R,5R,6S,7R,8S,9R,10S,13S)-7,8β-Epoxy-momilactone-A.

Project description:The title compound, C(20)H(26)O(4), was extracted from Leucas Urticifolia, a wild Lamiaceae herb distributed in the Punjab, Baluchistan, Sindh and the Rajputana desert of Pakistan. The plant is utilized for various medicinal applications by the local community. The title compound is based on the pimarane-diterpene skeleton. The mol-ecule exhibits an ep-oxy ring fused to momilactone-A, leading to a penta-cyclic mol-ecular structure. The absolute configuration was assigned by comparison with the crystal structure of momilactone, but needs further verification. The crystal structure is governed by four inter-molecular hydrogen-bond inter-actions of the C-H⋯O type.

| S-EPMC2961202 | biostudies-literature

(6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol.

Project description:The title compound, C(21)H(27)NO(2), exhibits hydrogen bonding between the phenolic H atom and the heterocyclic N atom. The absolute configuration of the mol-ecule is known from the synthetic procedure.

| S-EPMC2983802 | biostudies-literature

(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one.

Project description:The title compound, C(16)H(22)N(2)O(3), was synthesized during the course of a study on (1R,2S)-norephedrine-derived 1,3,4-oxadiazinan-2-ones. The conformation adopted by the isopropyl group is pseudo-axial relative to the oxadiazinan core. The allylic strain contributes to this conformational arrangement.

| S-EPMC2969394 | biostudies-literature

(1S,2R,3S,6S,7R)-3,7,11,11-Tetra-methyl-6,7-epoxybi-cyclo-[5.4.0]undecane-2-ol.

Project description:The title compound, C15H26O2, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the Atlas cedar (cedrus atlantica). The mol-ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The seven- and six-membered rings each have a twist-boat conformation. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the b-axis direction.

| S-EPMC4011231 | biostudies-literature

(2E,4R,5R,6S)-2-(4,5,6-Trihy-droxy-cyclo-hex-2-en-1-yl-idene)acetonitrile.

Project description:The crystal structure of the title compound, C(8)H(9)NO(3), is characterized by a complex three-dimensional hydrogen-bond network in which every mol-ecule is connected to six symmetry-related neighbours.

| S-EPMC3435749 | biostudies-literature