2309-32-2Relevant articles and documents
SYNTHESIS AND 13C-NMR ANALYSIS OF 5α- AND 5β-CHOLESTANE-3,6-DIONE
Wijnberg, Joannes B. P. A.,Groot, Aede de
, p. 333 - 344 (1989)
Starting from cholesterol a simple and efficient synthesis of 5α-cholestane-3,6-dione and 5β-cholestane-3,6-dione is described.The 13C shielding data of C-7, C-9, and C-19 in both isomers can be used in the determination of the stereochemistry at C-5 of these compounds.The combination of 13C NMR spectroscopy and the simple synthesis of both isomers offers good opportunities for the determination of the stereochemistry at C-5 of 3,6-dioxosteroids.
ELECTROOXIDATIVE SIMULATION OF STEREOSELECTIVITY IN MICROSOMAL ALLYLIC HYDROXYLATION
Shono, Tatsuya
, p. 91 - 94 (1984)
A comparison of the stereochemistry of liver microsomal γ-hydroxylation of some cyclic α,β-unsaturated ketones with that of electrochemical γ-acetoxylation of the corresponding dienol esters and with that of peracid oxidation of the dienol esters has been carried out.
Kurath,Capezzuto
, p. 3527 (1956)
Novel method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone as raw material
-
, (2021/11/19)
The invention provides a method for synthesizing cholesterol from 21-hydroxy-20-methylpregna-4-ene-3-ketone (4-BA) as a raw material. The method comprises the step of: (1) carrying out etherification reaction, oxidation reaction, Grignard reagent addition reaction, sulfonylation reaction, reduction reaction, acetylation reaction and reduction reaction on 4-BA and triethyl orthoformate to obtain cholesterol. The synthesis method is simple in process, high in yield, low in cost, environment-friendly in process and suitable for industrial production.
Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples
Bus, Katarzyna,Ofiara, Karol,Sitkowski, Jerzy,Szterk, Arkadiusz,Zmys?owski, Adam
, (2020/06/08)
It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.