190513-05-4

Basic information

• Product Name: (3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-methyl-2-(triphenyl-λ⁵-phosphanylidene)-ethyl]-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol
• CAS NO: 190513-05-4
• Molecular Weight: 610.817
• Mol File: 190513-05-4.mol

Chemical Properties

• CAS DataBase Reference: (3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-methyl-2-(triphenyl-λ⁵-phosphanylidene)-ethyl]-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-methyl-2-(triphenyl-λ⁵-phosphanylidene)-ethyl]-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol(190513-05-4)
• EPA Substance Registry System: (3R,5S,7R,8R,9S,10S,12S,13S,14S,17R)-10,13-Dimethyl-17-[(S)-1-methyl-2-(triphenyl-λ⁵-phosphanylidene)-ethyl]-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol(190513-05-4)

Safety Data

• Hazardous Substances Data: 190513-05-4(Hazardous Substances Data)

Upstream product

• 68777-19-5 24-norcholic acid triformate 
• 190513-02-1 3α,7α,12α-triformyloxy-22-iodo-23,24-bisnor-5β-cholane 
• 190513-03-2 3α,7α,12α-trihydroxy-22-iodo-23,24-bisnor-5β-cholane 
• 603-35-0 triphenylphosphine 
• 60696-62-0 24-norcholic acid 

Relevant articles and documents

A new chiral synthesis of bullfrog bile sterol 5β-ranol

(24R)-27-Nor-5β-cholestane-3α,7α,12α,24,26-pentol (5β-ranol) has been synthesised by the Wittig olefinic coupling of a steroidal module and a side-chain module followed by reduction and deprotection. The steroidal module is derived from cholic acid by a one-carbon degradation of the side chain to produce norcholic acid followed by the loss of a second carbon in an iododecarboxylation and then synthesis of the triphenylphosphonium iodide. The side-chain module is derived from (S)-(-)-butane-1,2,4-triol by benzylidene protection of the 2,4-diol followed by Swern oxidation to the aldehyde. This general synthetic scheme could be used to produce a range of bile sterols with the (24R)-hydroxy moiety which may have significant hepatoprotective activity against liver damage induced by free radicals or reactive metabolites.