21059-39-2

Upstream product

• 911-40-0 7-ketodeoxycholic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 7443-91-6 methyl cholate 3-acetate 
• 21066-20-6 methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) 
• 4651-67-6 7-Ketolithocholic acid 
• 10452-65-0 methyl 3α-acetoxy-7-oxo-5β-cholan-24-oate 
• 474-25-9 chenodeoxycholic acid 
• 128-13-2 ursodeoxycholic acid 
• 318473-26-6 Naphthalene-2-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-acetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-7-(2-oxo-2-phenyl-acetoxy)-hexadecahydro-cyclopenta[a]phenanthren-12-yl ester 
• 58822-33-6 methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate 

Relevant academic research and scientific papers

A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid

A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

Synthetic method of 7-keto-lithocholic acid

The invention discloses a chemical synthetic method of an intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, and belongs to the field of organic chemical synthesis. According to the chemical synthetic method of the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, cholic acid is adopted as a raw material, and through reactions of selective oxidization of 7alpha-hydroxyl, esterification of side chain carboxyl groups, esterification of 3alpha-hydroxyl, methanesulfonic acid esterification, elimination, hydrogenation, and hydrolysis of 12alpha-hydroxyl, the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid is synthesized. According to the chemical synthetic method of the intermediate 7-keto-lithocholic acid (3alpha-hydroxyl-7-ketone-5beta-cholestane-24-acid) of obeticholic acid, cheap cholic acid is adopted as the raw material, the synthesis method is novel, low in cost, high in yield and environmentally friendly, which facilitates industrialized production.

[...] synthetic method and intermediate (by machine translation)

The invention discloses a method for synthesizing [...], the cholic acid as the raw material, after 7 α - hydroxy selective oxidation, side chain carboxyl ester, 3 α - hydroxy ester, 12 α - hydroxy methanesulfonic acid esterification, eliminate, selective hydrolysis of 3 bit ester group, with the three-a chlorosilane reaction to produce the silicon ether, with acetaldehyde to aldol condensation, and the hydrolysis, catalytic hydrogenation reduction olefinic bond, carbonyl reduction reaction such as, to synthesize states the aobeiaobei cholic acid. The method of the invention uses cheap cholic acid as raw materials, synthetic method is novel, low cost, high yield, mild reaction conditions, easy post treatment, environmental friendly, convenient to industrial production. (by machine translation)

Chenodeoxycholic acid synthesis method

The invention discloses a chenodeoxycholic acid synthesis method, wherein cholic acid is used as a raw material, and 7[alpha]-hydroxyl selective oxidation, side-chain carboxyl esterification, 3[alpha]-hydroxyl esterification, 12[alpha]-hydroxymethanesulfonic acid esterification, elimination, hydrolysis, reduction and other reactions are performed to prepare the chenodeoxycholic acid. According to the present invention, the chenodeoxycholic acid synthesis method has advantages of simple step, less side reaction, high yield and easily available raw materials, is suitable for industrial production, can solve the problems of high synthesis cost, low yield and the like in the prior art, and is suitable for industrial mass-production.

A synthesis method of ursodeoxycholic acid (by machine translation)

The invention discloses a method for synthesizing of ursodeoxycholic acid, the cholic acid as the raw material, after 7 α - hydroxy selective oxidation, side chain carboxyl ester, 3 α - hydroxy ester, 12 α - hydroxy methanesulfonic acid esterification, elimination, hydrolysis, reduction of synthesis of ursodeoxycholic acid. The invention of ursodeoxycholic acid synthesis method, simple steps, less side reaction, high yield, raw materials are easy, is suitable for industrial production, solved in the prior art synthesis cost high, the yield is low and the like, and has a wide application. (by machine translation)

SYNTHESIS OF MONOSULFATES OF CHOLIC ACID DERIVATIVES

The 3-, 7- and 12-monosulfates of bile acids having an oxo or acetoxy group on the steroid nucleus have been synthesized.Cholic acid derivatives appropriately protected were sulfated with chlorosulfonic acid and pyridine in the usual manner.The utilization of partial acetylation and hydrolysis together with chromium trioxide oxidation and sodium borohydride reduction provided the disired sulfates of cholic acid derivatives in satisfactory yields.The nuclear magnetic resonance spectral properties of the bile acid derivatives are briefly discussed.Keywords - sulfation; bile acid monosulfate; partial acetylation; cholic acid monoacetate; 3-dehydrocholate; 7-dehydrocholate; 12-dehydrocholate