897-01-8Relevant articles and documents
Synthesis of sodium androst-5-ene-17-one-3β-methylene sulfonate
Vhu, Guo-Hua,Li, Pui-Kai
, p. 543 - 545 (1997)
The synthesis of sodium androst-5-ene-17-one-3β-methylene sulfonate 2, a stable analog of memory-enhancing neurosteroid dehydroepiandrosterone sulfate, is described.The synthesis of compound 2 is carried out in six steps from dehydroepiandrosterone. - Keywords: steroids; steroid sulfatase; memory enhancement; dehydroepiandrosterone sulfate
Stereoretentive chlorination of cyclic alcohols catalyzed by titanium(IV) tetrachloride: Evidence for a front side attack mechanism
Mondal, Deboprosad,Li, Song Ye,Bellucci, Luca,Laino, Teodoro,Tafi, Andrea,Guccione, Salvatore,Lepore, Salvatore D.
, p. 2118 - 2127 (2013/04/10)
A mild chlorination reaction of alcohols was developed using the classical thionyl chloride reagent but with added catalytic titanium(IV) chloride. These reactions proceeded rapidly to afford chlorination products in excellent yields and with preference for retention of configuration. Stereoselectivities were high for a variety of chiral cyclic secondary substrates including sterically hindered systems. Chlorosulfites were first generated in situ and converted to alkyl chlorides by the action of titanium tetrachloride which is thought to chelate the chlorosulfite leaving group and deliver the halogen nucleophile from the front face. To better understand this novel reaction pathway, an ab initio study was undertaken at the DFT level of theory using two different computational approaches. This computational evidence suggests that while the reaction proceeds through a carbocation intermediate, this charged species likely retains pyramidal geometry existing as a conformational isomer stabilized through hyperconjugation (hyperconjomers). These carbocations are then essentially "frozen" in their original configurations at the time of nucleophilic capture.
Chlorination of 3β-hydroxyl-5-Δ steroids with anhydrous ferric chloride
Liu, Feng-Wu,Liu, Hong-Min,Zhang, Yan-Bing,Zhang, Jing-Yu,Tian, Li-Huan
, p. 825 - 830 (2007/10/03)
Treatment of 3β-hydroxyl-5-Δ steroids with anhydrous FeCl 3 in CH2Cl2 afforded reasonable yields of the corresponding alkyl chlorides with a retention of configurations. The structures of the chlorine-exchanging products were determined by NMR and HRMS spectra. The absolute configurations were confirmed by X-ray crystal analysis of 3β-chloro-androst-5-en-17-one. The generality and scope of the reaction were also investigated.