10573-17-8Relevant articles and documents
Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6,-dihydroxy-and 6-hydroxy-5α-cholanoic acids
Iida, Takashi,Tamaru, Tamaaki,Chang, Frederic C.,Niwa, Toshifumi,Goto, Junichi,Nambara, Toshio
, p. 362 - 369 (1993)
An improved procedure for the syntheses of stereoisomeric 3,6,-dihydroxy- and 6-hydroxy-5α-cholanoic acids (and their methyl esters) is described. The principal reactions emplyoed are those reported in the preceding paper of this series, with the commercially available hyodeoxycholic acid as starting material. The final step in the procedure is the reduction of the key 5α C-6 ketones with either the stereoselective equatorial reagent, Li/NH3/MeOH, or the axial reagent, Zn(BH4)2). The results of analysis of the prepared 6-monohydroxylated and 3,6-dihydroxylated stereoisomers by thin-layer chromatographic, high performance liquid chromatographic and gas-liquid chromatographic mobilities, and 1H and 13C nuclear magnetic resonance spectra are discussed along with the dat for the corresponding compounds in the 5β-series. (Steroids 58: 362-369, 1993).
Preparation method of 3-hydroxy-6-ketocholanic acid with low cost and high yield
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Paragraph 0036-0041, (2020/06/20)
The invention discloses a preparation method of 3 alpha-hydroxy-6-keto-5 beta-cholestane-24-acid with low cost and high yield, which is characterized by comprising the following steps: adding hyodeoxycholic acid into a mixed solution of an organic solvent and water, and stirring to dissolve; adding bromide and acid, stirring and dissolving; bromate is added for reaction; adding a terminating agent, and stirring to terminate the reaction; adding water to crystallize the product; and carrying out solid-liquid separation, washing a solid product with water for multiple times, and drying to obtainthe 3 alpha-hydroxy-6-keto-5 beta-cholestane-24-acid. According to the method, a common and safe reagent is adopted, the hyodeoxycholic acid is selectively oxidized into the 3 alpha-hydroxy-6-keto-5beta-cholestane-24-acid under a relatively mild condition, the product purity is greater than 98.0%, and the yield is greater than 85%. The method has the advantages of cheap reagents, simple operation, high process reproducibility, simple post-treatment, high product purity and high yield, and can easily implement industrial production.
Method for synthesizing lithocholic acid from hyodesoxycholic acid
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Paragraph 0036; 0037; 0038; 0039, (2017/08/29)
The invention discloses a method for synthesizing lithocholic acid, comprising: using hyodesoxycholic acid as a start material, and performing two-step reaction of 6Alpha-OH selective oxidation and Huang Minglon reduction to synthesize the lithocholic acid. The start material herein is low in price and easy to obtain, the synthetic steps are short, posttreatment is simple, few side reactions are employed, and the method is applicable to industrial production.
