37772-32-0

Usage

InChI:InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h14,18-24,28H,6-13,15-17H2,1-5H3/t19-,20+,21-,22+,23-,24+,26+,27-/m1/s1

Upstream product

• 54055-98-0 3-Iodo-benzoic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 80-97-7 Cholestanol 
• 75415-38-2 (5R,8S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 187478-17-7 3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-9-thiocyanato-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 81095-64-9 C₈₅H₁₄₄O₃SSi 
• 101836-11-7 Nicotinic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 114682-97-2 9-Oxo-9H-thioxanthene-3-carboxylic acid (3R,5R,8S,9R,10S,13R,14S,17R)-9-chloro-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 

Downstream Products

• 334699-47-7 (3R,5S,8S,10S,13R,14S,17R)-3-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 
• 143539-78-0 4'-Iodo-biphenyl-3-carboxylic acid (3R,5S,8S,9R,10S,13S,14S)-9-fluoro-10,13-dimethyl-11,17-dioxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 143539-77-9 4'-Iodo-biphenyl-3-carboxylic acid (3R,5S,8S,9R,10S,11S,13S,14S)-11-acetoxy-9-fluoro-10,13-dimethyl-17-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 143539-75-7 4'-Iodo-biphenyl-3-carboxylic acid (3R,5S,8S,9R,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-9-fluoro-10,13-dimethyl-11-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 143539-74-6 4'-Iodo-biphenyl-3-carboxylic acid (3R,5S,8S,9R,10S,11S,13R,14S,17R)-11-acetoxy-17-((R)-1,5-dimethyl-hexyl)-9-fluoro-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 75415-47-3 9β-hydroxy-9,10-secocholesta-1,3,5(10)-triene 
• 75415-47-3 9α-hydroxy-9,10-secocholesta-1,3,5(10)-triene 
• 75415-52-0 C₂₉H₄₆S₂ 
• 75415-49-5 9,10-seco-1,3,5⁽¹⁰⁾-cholestatrien-9-one 
• 75477-04-2 (1R,3aS,4S,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-4-((E)-2-o-tolyl-vinyl)-octahydro-indene 
• 75415-53-1 (1R,3aS,4S,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-4-(2-o-tolyl-ethyl)-octahydro-indene 
• 334699-61-5 [(3R,5S,8S,9S,10S,11R,13R,14S,17R)-3-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-yloxy]-tert-butyl-dimethyl-silane 
• 334699-49-9 (3R,5S,8S,9S,10S,11R,13R,14S,17R)-3-Benzyloxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-ol 

Relevant academic research and scientific papers

A synthetic approach towards stoloniferones: Synthesis of 11-acetyl-24-desmethyl-stoloniferone C

The synthesis of 11α-acetoxy-5β,6β-epoxycholest-2-en-1-one, a compound containing the nuclear functionalities of the stoloniferones, is described starting from dihydrocholesterol.

Remote functionalization by tandem radical chain reactions

Normal radical relay chlorination of cholestan-3α-ol directed by an attached m-iodobenzoate ester group affords a 9α-chloro steroid, but when the same reaction is conducted in the presence of an excess of CBr4 the product is a 9α-bromo steroid. Similarly, when the same radical relay reaction is carried out in the presence of an excess of (SCN)2 rather than CBr4, the product is a 9α-thiocyano steroid. Several other examples of these reactions have been developed. These tandem remote functionalization reactions succeed because an intramolecular hydrogen abstraction by a complexed-chlorine atom generates a specific substrate radical in each case. Copyright 1997 by the Royal Society Chemistry.

Chemical degradation of steroid side chains. Efficient conversion of cholestanol to corticosteroid intermediates.

17-Chlorosteroids, produced by template-directed halogenation of 9-fluoro 11-oxygenated cholestanols that are themselves produced by template methods, are converted to their 17-keto analogs in high yields (85-91%) after HCl elimination with DBU, followed by ozonolysis.

THE THIOXANTHONE SYSTEM AS A TEMPLATE IN FREE RADICAL RELAY CHLORINATION OF A STEROID

The 3-α-cholestanyl ester of thioxanthone-3-carboxylic acid undergoes selective chlorination of the steroid C-9 carbon by a radical relay mechanism directed by the thioxanthone template.

High Pressure Liquid Chromatography of Sterol Benzoates

The high pressure liquid chromatographic behavior of forty sterol benzoates on a Zorbax ODS reverse phase column and on a normal phase column of Zorbax SIL is desrcibed.Keywords-HPLC; sterol benzoate; cholestadienol; phytosterol.