84965-66-2

Usage

InChI:InChI=1/C27H40O7/c1-17(5-4-10-28)20-6-7-21-25-22(13-24(34-16-31)27(20,21)3)26(2)9-8-19(32-14-29)11-18(26)12-23(25)33-15-30/h10,14-25H,4-9,11-13H2,1-3H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 74670-08-9 (3α,5β,7α,12α)-3,7,12-tris(formyloxy)cholan-24-oyl chloride 
• 2097-89-4 cholic acid triformate 
• 127656-72-8 Formic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diformyloxy-17-((R)-4-imidazol-1-yl-1-methyl-4-oxo-butyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 96736-29-7 3α,7α,12α-triformyloxy-5β-24-hydroxy-cholane 

Downstream Products

• 144210-47-9 methyl (E)-3α,7α,12α-trihydroxy-5β-cholest-24-en-26-oates 
• 144210-47-9 methyl (Z)-3α,7α,12α-trihydroxy-5β-cholest-24-en-26-oate 
• 5226-26-6 3α,7α,12α-Trihydroxy-5β-cholesten-24-26-saeure 
• 1061-64-9 3α,7α,12α,24ξ-tetrahydroxy-5β-cholestan-26-oic acid 

Relevant academic research and scientific papers

IMPROVED SYNTHESIS OF 5β-CHOLESTANE-3α,7α,12α,26(27)-TETROL ISOMERS FROM CHOLIC ACID

Synthesis of a mixture of the 25(R) and 25(S) isomers of 5β-cholestane-3α,7α,12α,26(27)-tetrol from cholic acid in four steps, including a Wittig reaction, is described.

IMPROVED SYNTHESIS OF 3α,7α,12α,24ξ-TETRAHYDROXY-5β-CHOLESTAN-26-OIC ACID

This paper describes three simple and short methods for the conversion of cholic acid into cholylaldehyde with protected hydroxyl groups.The first method involves lithium aluminium hydride reduction of the tetrahydropyranyl ether of methyl cholate and oxidation of the resulting primary alcohol with pyridinium chlorochromate.The second method employs diborane for the reduction of the -COOH group to the -CH2OH group, while the third method involves the reduction of 3α,7α,12α-triformyloxy-5β-cholan-24-oic acid (as the acid chloride) directly into 3α,7α,12α-triformyloxy-5β-cholan-24-al with TMA-ferride (tetramethylammonium hydridoirontetracarbonyl).The aldehyde obtained by any of the above methods underwent smooth Reformatsky reaction with ethyl α-bromopropionate to yield 3α,7α,12α,24ξ-tetrahydroxy-5β-cholestan-26-oic acid.