146276-36-0

Basic information

• Product Name: 20R 23S 24S-DINOSTERANE
• Synonyms: 20R 23S 24S-DINOSTERANE;ALPHA, ALPHA, ALPHA 20R 23S 24S 4A,23,24-TRIMETHYLCHOLESTANE
• CAS NO: 146276-36-0
• Molecular Formula: C30H54
• Molecular Weight: 414.757
• Mol File: 146276-36-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 20R 23S 24S-DINOSTERANE(CAS DataBase Reference)
• NIST Chemistry Reference: 20R 23S 24S-DINOSTERANE(146276-36-0)
• EPA Substance Registry System: 20R 23S 24S-DINOSTERANE(146276-36-0)

Safety Data

• Hazardous Substances Data: 146276-36-0(Hazardous Substances Data)

Upstream product

• 148552-88-9 (20R,23S,24S)-5α-dinosteran-29-ol tert-butyldimethylsilyl ether 
• 146201-25-4 Thiocarbonic acid O-phenyl ester O-[(4S,5S,8R,9S,10R,13S,14S,17S)-4,10,13-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester 
• 146201-38-9 4-Methyl-3-methylene-2-[(R)-2-((4R,5S,8S,9S,10S,13R,14S,17R)-4,10,13-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-propyl]-pentanoic acid methyl ester 
• 146276-30-4 (4S,5S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-4,10,13-trimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 146201-24-3 (4S,5S,8R,9S,10R,13S,14S,17S)-4,10,13-Trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-ol 
• 978-98-3 20-ethylenedioxy-4-pregnen-3-one 
• 122405-69-0 4α-methyl-5α-stigmast-22t-en-3-one 
• 148552-73-2 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate 
• 148552-72-1 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal 
• 145-13-1 Pregnenolone 
• 563-80-4 3-methyl-butan-2-one 
• 148459-79-4 (20R,23S,24S)-5α-dinosteran-29-ol mesylate 
• 146201-42-5 (20R,23S,24S)-5α-Dinosteran-29-ol 
• 146201-31-2 (20S)-20-(iodomethyl)-4α-methyl-5α-pregnane 

Relevant articles and documents

Synthesis of Biological Markers in Fossil Fuels. 7. Selected Diastereomers of 4α-Methyl-5α-stigmastane and 5α-Dinosterane

Efficient routes for the preparation of selected C-23 and C-24 diastereomers of the C30 biological markers 4α-methyl-5α-stigmastane (1) and 5α-dinosterane (2) involved the alkylation of 20-(iodomethyl)-4α-methyl-5α-pregnane with either saturated or α,β-unsaturated esters.The alkylation of (20S)-20-(iodomethyl)-4α-methyl-5α-pregnane with methyl (3R)-3-ethyl-4-methylpentanoate furnished methyl (20R,23ξ,24S)-4α-methyl-5α-stigmastane-23-carboxylate, and a subsequent decarbomethoxylation provided (20R,24R)-1.The alkylation of (20S)-20-(iodomethyl)-4α-methyl-5α-pregnane with methyl (3S)-3,4-dimethylpentanoate led to methyl (20R,23ξ,24R)-4α,24-dimethyl-5α-cholestane-23-carboxylate, and the reduction of this mixture provided principally (20R,23S,24R)-5α-dinosteran-29-ol.The further reduction of the mesylate of this isomer secured (20R,23S,24R)-5α-dinosterane (2a).The application of the same sequence of reactions using methyl (3R)-3,4-dimethylpentanoate led principally to (20R,23R,24S)-5α-dinosterane (2d).The alkylation of (20S)-20-(iodomethyl)-4α-methyl-5α-pregnane with methyl (2ξ)-3,4-dimethyl-2-pentanoate and a subsequent reduction of the ester provided a separable mixture of (20R,23R)- and (20R,23S)-5α-dinoster-24(28)-en-29-ol in a 2.4:1 ratio.The conversion of (20R,23R)-5α-dinoster-24(28)-en-29-ol to the corresponding tert-butyldimethylsilyl ether, reduction of the Δ24(28) bond with hydrogen over platinum oxide, and deprotection gave principally (20R,23R,24R)-5α-dinosteran-29-ol.The further reduction of this alcohol provided (20R,23R,24R)-5α-dinosterane (2b).The application of the same sequence of reactions to (20R,23S)-5α-dinoster-24(28)-en-29-ol provided (20R,23S,24S)-5α-dinosterane (2c).Diastereoselectivity at the C-23 position in these ester alkylations was examined as a function of stereochemistry at both the C-20 and C-24 positions.