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β-Sitosterol-d7 (Mixture of Diastereomers)

目录号 : GC20143

β-Sitosterol-d7 (Mixture of Diastereomers) Chemical Structure

Cas No.:2260669-28-9

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Chemical Properties

Cas No. 2260669-28-9 SDF
分子式 C29H43D7O 分子量 421.75
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1 mM 2.3711 mL 11.8554 mL 23.7107 mL
5 mM 0.4742 mL 2.3711 mL 4.7421 mL
10 mM 0.2371 mL 1.1855 mL 2.3711 mL
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Research Update

2,4-Alkadienal trapping by phenolics

Food Chem 2018 Oct 15;263:89-95.PMID:29784333DOI:10.1016/j.foodchem.2018.04.121.

Phenolics can trap lipid-derived reactive carbonyls as a protective function that diminishes the broadcasting of the lipid oxidative damage to food macromolecules. In an attempt to clarify the trapping of 2,4-alkadienals by phenolics, this study analyzes the reactions of 2,4-hexadienal, 2,4-heptadienal, and 2,4-decadienal with 2-methylresorcinol. These reactions produced (E)-4-(alk-1-en-1-yl)-8-methyl-2,7-bis(prop-1-en-2-yloxy)chromanes, which were isolated and characterized by 1D and 2D NMR and MS. Carbonyl-phenol adduct formation was favored at pH > 7 and moderate temperatures (25-80 °C). Adducts were quantified and shown to be produced as a Mixture of Diastereomers. Diastereomers 2R,4S plus 2S,4R were formed to a higher extent than diastereomers 2R,4R plus 2S,4S under the different conditions assayed, although activation energies (Ea) for the formation of all of them was mostly the same (∼62 kJ·mol-1). These results show that phenolics can trap 2,4-alkadienals and provide the basis for the later detection of the formed adducts in food pro[ducts.

Directing-Group-Assisted Manganese-Catalyzed Cyclopropanation of Indoles

Org Lett 2019 Apr 5;21(7):2025-2028.PMID:30860389DOI:10.1021/acs.orglett.9b00150.

The first manganese-catalyzed cyclopropanation of indoles is reported in moderate to excellent yield with methyl-2-diazo-2-arylacetates. This new strategy involved acetyl (COCH3) as the directing group and exhibited exceptional functional group tolerance. In the absence of stereodirecting groups the desired products were obtained as a Mixture of Diastereomers (7:3 → 8:2). Control experiments and DFT studies elucidated the probable pathway for the formation of cyclopropane-fused indole product. Deacetylation of the final products afforded both C3-substituted NH-indoles.

Single-scan ultra-selective 1D total correlation spectroscopy

Chem Commun (Camb) 2021 Mar 7;57(19):2368-2371.PMID:33533774DOI:10.1039/d0cc08033k.

Selective 1D TOCSY is a powerful tool in the assignment of NMR spectra of organic molecules. Here an order of magnitude improvement in selectivity, allowing overlapping multiplets to be excited separately, is achieved in a single scan using the very recent GEMSTONE method. The new experiment is illustrated using an antibiotic and a Mixture of Diastereomers.

Experimental Determination and Theoretical Calculation of the Eutectic Composition of Cefuroxime Axetil Diastereomers

AAPS PharmSciTech 2017 Oct;18(7):2570-2578.PMID:28229357DOI:10.1208/s12249-017-0739-8.

Cefuroxime axetil (CFA), an ester prodrug of cefuroxime exists as a pair of diastereoemers, namely isomer A and isomer B. To enable phase diagram construction, crystallization of the diastereomers of CFA from the commercially available amorphous drug substance was carried out. Isomer A was separated with a purity approaching 100% whereas the maximum purity of isomer B was 85% as confirmed by solution state proton NMR spectroscopy. The crystalline forms of isomer A and isomer B were confirmed as forms AI and BI, respectively, based on differential scanning calorimetry (DSC) analysis and powder X-ray diffraction. DSC analysis was used to observe the melting behavior of different diastereomer mixture compositions. The binary solid-liquid phase diagram for mixture compositions ranging from 0 to 85% w/w isomer B indicated the formation of a eutectic mixture having a melting temperature of 124.7 ± 0.4°C and a composition of 75% w/w (+/-5% wt.) isomer B. The eutectic composition was calculated using an index based on the van't Hoff equation for melting point depression and was found to be 75% isomer B and 25% isomer A. As CFA is present in commercial preparations as a Mixture of Diastereomers, the formation of a eutectic mixture between the diastereomers may impact the solubility and stability of the commercial product. Eutectic formation can be explained on the basis of the chemical similarity of diastereomers that favor miscibility in the liquid state.

Visible Light-Mediated, Highly Diastereoselective Epimerization of Lactams from the Most Accessible to the More Stable Stereoisomer

ACS Catal 2022 Jul 1;12(13):7798-7803.PMID:PMC9273106DOI:10.1021/acscatal.2c02232.

Most known methods to access δ-lactams with stereogenic centers at the α- and β-positions are highly selective for the contra-thermodynamic syn diastereomer, typically via hydrogenation of the corresponding pyridinones or quinolinones. We describe here the development of a photoredox-mediated hydrogen atom transfer (HAT) approach for the epimerization of δ-lactams to access the more stable anti diastereomers from the contra-thermodynamic syn isomers. The reaction displays broad functional group compatibility, including acid, ester, 1°, 2° and 3° amide, carbamate, and pyridyl groups, and was effective for a range of differently substituted monocyclic and bicyclic lactams. Experimentally observed diastereoselectivities are consistent with the calculated relative stabilities of lactam diastereomers. Convergence to the same diastereomer ratio from the syn- and anti- diastereomers establishes that reversible epimerization provides an equilibrium Mixture of Diastereomers. Additionally, deuterium labeling and luminescence quenching studies shed further light on the mechanism of the reaction.