96475-64-8

Usage

Uses

Used in Pharmaceutical Industry:
(3α,5β)-3-[(Ethoxycarbonyl)oxy]-7-oxo-cholan-24-oic Acid Methyl Ester is used as an intermediate in the synthesis of α-Muricholic Acid (M732750), a bile acid metabolite found in urine. This metabolite has potential applications in the development of drugs targeting bile acid metabolism and related disorders, such as cholestasis, gallstone formation, and liver diseases.
Used in Diagnostic Applications:
α-Muricholic Acid, synthesized using (3α,5β)-3-[(Ethoxycarbonyl)oxy]-7-oxo-cholan-24-oic Acid Methyl Ester, can be used as a biomarker for monitoring bile acid metabolism and liver function. Its detection in urine can provide valuable information for diagnosing and managing liver-related conditions.
Used in Research and Development:
(3α,5β)-3-[(Ethoxycarbonyl)oxy]-7-oxo-cholan-24-oic Acid Methyl Ester serves as a valuable compound for research purposes, particularly in the field of organic chemistry and drug discovery. Its unique structure and functional groups make it an interesting target for the development of new synthetic methods and the exploration of its potential biological activities.

Upstream product

• 61252-49-1 methyl 3α-(ethoxycarbonyloxy)-7α-(hydroxyl)-5β-cholanoate 
• 10538-59-7 7-ketolithocholic methyl ester 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 4651-67-6 7-Ketolithocholic acid 
• 66225-78-3 glycoβ-muricholic acid 
• 96475-68-2 C₃₅H₅₂N₂O₇S 

Relevant academic research and scientific papers

Synthetic method for obeticholic acid intermediate

The invention discloses a synthetic method for an obeticholic acid intermediate. The method includes the steps that organic solvent is poured into a reactor protected by inert gas, 3 alpha-hydroxyl-7-keto-5beta-cholane-24-oate is dissolved into the organic solvent, and then organic alkali is added; the solution is cooled to 0 DEG C-5 DEG C, then carbonate is slowly added dropwise to protect the 3-position hydroxyl group, after dropwise addition is completed, the reaction solution is heated to 20 DEG C-50 DEG C and is stirred for 2-8 h, and then the organic solvent is removed through decompression concentration; ice water is added for dissolution, ethyl acetate is added to extract the water phase, organic layers are combined and washed, an appropriate amount of anhydrous sodium sulfate is adopted for drying so that the organic layers are concentrated, and the obeticholic acid intermediate is obtained. The 3-position hydroxyl group is protected with carbonate first, the 7-position carbonyl enol is protected in a trimethylsilylation mode, the dosage of LDA is reduced by a half, and the efficiency of the condensation reaction is higher.

INHIBITORS OF THE FARNESOID X RECEPTOR AND USES IN MEDICINE

Disclosed are inhibitors of the farnesoid X receptor, for example of formula (I), wherein R1, R2, R4, X, Y, Z, m, and n are as defined herein, which are useful in treating or preventing obesity, type 2 diabetes/insulin resistance and non alcoholic fatty liver disease in a mammal in need thereof. Also disclosed is a composition comprising a pharmaceutically suitable carrier and at least one compound of the invention, a method of method of inhibiting a farnesoid X receptor in a mammal, and a method of treating or preventing obesity in a mammal.

Chemical synthesis of 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid: An internal standard for mass spectrometric analysis of the abnormal Δ5-bile acids occurring in Niemann-Pick disease

In Niemann-Pick disease, type C1, increased amounts of 3β,7β-dihydroxy-5-cholenoic acid are reported to be present in urinary bile acids. The compound occurs as a tri-conjugate, sulfated at C-3, N-acetylglucosamidated at C-7, and N-acylamidated with taurine or glycine at C-24. For sensitive LC-MS/MS analysis of this bile acid, a suitable internal standard is needed. We report here the synthesis of a satisfactory internal standard, 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid (as the disodium salt). The key reactions involved were (1) the so-called "second order" Beckmann rearrangement (one-carbon degradation at C-24) of hyodeoxycholic acid (HDCA) 3,6-diformate with sodium nitrite in a mixture of trifluoroacetic anhydride and trifluoroacetic acid, (2) simultaneous inversion at C-3 and elimination at C-6 of the ditosylate derivatives of the resulting 3α,6α-dihydroxy-24-nor-5β-cholanoic acid with potassium acetate in aqueous N,N-dimethylformamide, and (3) regioselective sulfation at C-3 of an intermediary 3β,7β-dihydroxy-24-nor-Δ5 derivative using sulfur trioxide-trimethylamine complex. Overall yield of the desired compound was 1.8% in 12 steps from HDCA.