27460-26-0Relevant academic research and scientific papers
A new synthesis of cerebrosterol and its 24-epimer from lithocholic acid
Khripach,Zhabinskii,Antonchik
, p. 258 - 262 (2007)
A new method for the synthesis of both isomers of 24-hydroxycholesterol starting from lithocholic acid is proposed.
A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol
Zhao, Qian,Qian, Chao,Chen, Xin-Zhi
, p. 16 - 21 (2016)
A new highly stereoselective construction of the side chain of the C-24 and C-25 oxysterols has been achieved by using desmosterol acetate as the starting material and an improved Sharpless catalytic asymmetric dihydroxylation with 100% d.e. (diastereomeric excess) as the key step. The result is much better than the usual asymmetric dihydroxylation procedure. t-Butyl nitrite/2,2,6,6-tetramethylpiperidine N-oxyl radical/FeCl3 catalyst system was developed to activate molecular oxygen for the aerobic oxidation of 24-hydroxycholesterol and the 24-ketocholesterol was obtained in 86.2% yield. The oxidation system has never been reported before. The mechanism for the catalytic aerobic oxidation was also proposed.
Stereoselective Synthesis of Squalamine Dessulfate
Moriarty, Robert M.,Enache, Livia A.,Kinney, William A.,Allen, Craig S.,Canary, James W.,et al.
, p. 5139 - 5142 (2007/10/02)
Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol.The key step is establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-met
A Stereoselective Synthesis and a Convenient Synthesis of Optically Pure (24 R)- and (24 S)-24-hydroxycholesterols
Koch, Patrick,Nakatani, Yoichi,Luu, Bang,Ourisson, Guy
, p. 185 - 194 (2007/10/02)
A new stereoselective synthesis of optically pure (24 S)-24-hydroxycholesterol (cerebrosterol) and (24 R)-24-hydroxycholesterol, using D- and L-valines as chiral sources, as well as a convenient synthesis, are described.
Stereoselective Synthesis of (22R)- and (22S)-22-Methylcholesterol
Zielinski, Jan,Li, Hui-ting,Djerassi, Carl
, p. 620 - 625 (2007/10/02)
22-Methylcholesterol, though hitherto unknown, is likely to exist in nature in the marine environment.In order to facilitate its eventual recognition, stereoselective syntheses of the 22R and 22S isomers of 22-methylcholesterol were developed by using the
Chirality Transfer in the Cholesterol Side Chain; Synthesis of (24R)- and (24S)-24-Hydroxycholesterols
Takatsuto, Suguru,Ishiguro, Masaji,Ikekawa, Nobuo
, p. 258 - 260 (2007/10/02)
Δ23-22-Acetoxycholesterol derivatives can be converted into 24-hydroxycholesterol derivatives highly stereoselectively by 1,3-chirality transfer with bis(acetonitrile)palladium(II) dichloride.
