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.
Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids
Rozatian, Neshat,Harsanyi, Antal,Murray, Ben J.,Hampton, Alexander S.,Chin, Emily J.,Cook, Alexander S.,Hodgson, David R. W.,Sandford, Graham
supporting information, p. 12027 - 12035 (2020/08/28)
Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6-position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N?F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β-fluoroprogesterone to the more pharmacologically active 6α-fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.