1778-02-5Relevant articles and documents
Oxygen-functionalization of C13-angular methyl group in pregnane steroid by means of intramolecular carbony-mediated anodic oxidation
Shibuya,Murakami,Shimada,Yoshikawa,Kitagawa
, p. 1143 - 1147 (1992)
An oxygen-functionalization of the C13-angular methyl group in 3β-acetoxy-5α-pregnan-20-one and its tetra-O-acetyl-β-D-glucopyranosyl derivative has been effected by means of an anodic oxidation mediated by the C20-carbonyl residue in the steroid skeleton.
-
Heyl,Herr,Centolella
, p. 247 (1949)
-
Ammonium formate/palladium on carbon: A versatile system for catalytic hydrogen transfer reductions of carbon-carbon double bonds
Paryzek, Zdzislaw,Koenig, Hanna,Tabaczka, Bartlomiej
, p. 2023 - 2026 (2003)
Various carbon-carbon double bonds in olefins and α,β -unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence of Pd/C as catalyst in refluxing methanol.
A Mild and Efficient Method for the Reduction of Oximes to Imines for Further in situ Reactions
Barton, Derek H. R.,Motherwell, William B.,Simon, Ethan S.,Zard, Samir Z.
, p. 337 - 338 (1984)
Tributylphosphine-diphenyl disulphide is an effective and mild reagent for reducing oximes to imines.
Convenient synthesis of new pregnenolone oximinyl oxalate dimers
Nahar,Sarker,Turner
, p. 315 - 318 (2008)
Three new symmetrical pregnenolone oxyminyl oxalate dimers (8-10) were synthesized from the corresponding pregnenolone oximes (3, 5, and 7) at room temperature. All dimers were characterised by spectroscopic means, notably HRFABMS and comprehensive NMR spectroscopic data analyses.
Chaudhuri,Gut
, p. 3737,3743 (1965)
Chemical synthesis of 7α-hydroxypregnenolone, a neuroactive steroid that stimulates locomotor activity
Yoshimoto, Francis K.,Arman, Hadi D.,Griffith, Wendell P.,Yan, Fangzhi,Wherritt, Daniel J.
, p. 50 - 57 (2017)
7α-Hydroxypregnenolone is an endogenous neuroactive steroid that stimulates locomotor activity. A synthesis of 7α-hydroxypregnenolone from pregnenolone, which takes advantage of an orthogonal protecting group strategy, is described. In detail, the C7-position was oxidized with CrO3 and 3,5-dimethylpyrazole to yield a 7-keto steroid intermediate. The resulting 7-ketone was stereoselectively reduced to the 7α-hydroxy group with lithium tri-sec-butylborohydride. In contrast, reduction of the same 7-ketone intermediate with NaBH4 resulted in primarily the 7β-hydroxy epimer. Furthermore, in an alternative route to the target compound, the 7α-hydroxy group was successfully incorporated by direct C–H allylic benzoyloxylation of pregnenolone-3-acetate with CuBr and tert-butyl peroxybenzoate followed by saponification. The disclosed syntheses to 7-oxygenated steroids are amenable to potentially obtain other biologically active sterols and steroids.
-
Marker et al.
, p. 1276,1278 (1942)
-
TRANSFORMED STEROIDS. 113. CYCLOBUTENOPREGNANES IN CYCLOADDITION AND OXIDATION REACTIONS
Kamernitskii, A. V.,Ignatov, V. N.,Levina, I. S.,El'yanov, B. S.
, p. 1375 - 1377 (1980)
-
REACTION OF SOME TRISUBSTITUTED STEROID EPOXIDES WITH TRIPHENYLPHOSPHINE - IODINE DOMPLEX. DEOXYGENATION OF EPOXIDES
Paryzek, Zdzislaw,Wydra, Roman
, p. 2601 - 2604 (1984)
Triphenylphosphine - iodine complex was found to be an effective reagent for deoxygenation of trisubstituted steroidal epoxides.The mechanism of the reaction is proposed.
Uvarova et al.
, p. 79,85 (1973)
SYNTHESIS OF 19-HYDROXYSTEROIDS II. NEW SYNTHESIS OF 19-HYDROXYPROGESTERONE
Kovganko, N. V.,Kashkan, Zh. N.,Chernov, Yu. G.
, p. 589 - 592 (1992)
19-Hydroxyprogesterone has been synthesized in seven stages from pregnenolone with an overall yield of 11percent.
Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
supporting information, p. 2498 - 2504 (2021/04/13)
The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
Steroid compound as well as preparation method and application thereof (by machine translation)
-
Paragraph 0058-0059; 0060-0061, (2020/10/29)
The compounds have the structure shown in the general formula (I) or the general formula (II); and experiments prove that the compounds can treat three-negative breast cancer by promoting apoptosis. (by machine translation)