80115-48-6

Basic information

• Product Name: (20S)-23,24-dinorchola-5,16-diene-3β,22-diyl 22-acetate 3-(toluene-p-sulfonate)
• Synonyms: (20S)-23,24-dinorchola-5,16-diene-3β,22-diyl 22-acetate 3-(toluene-p-sulfonate)
• CAS NO: 80115-48-6
• Molecular Weight: 526.737
• Mol File: 80115-48-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (20S)-23,24-dinorchola-5,16-diene-3β,22-diyl 22-acetate 3-(toluene-p-sulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: (20S)-23,24-dinorchola-5,16-diene-3β,22-diyl 22-acetate 3-(toluene-p-sulfonate)(80115-48-6)
• EPA Substance Registry System: (20S)-23,24-dinorchola-5,16-diene-3β,22-diyl 22-acetate 3-(toluene-p-sulfonate)(80115-48-6)

Safety Data

• Hazardous Substances Data: 80115-48-6(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 22953-07-7 (3S,8S,9S,10R,13S,14S,Z)-17-ethylidene-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 
• 108-24-7 acetic anhydride 
• 80115-47-5 (Z)-pregna-5,17(20)-dien-3β-yl toluene-p-sulfonate 
• 50-00-0 formaldehyd 
• 53-43-0 dehydroepiandrosterone 
• 139871-19-5 (3β,17Z)-3-{[(tert-butyl)dimethylsilyl]oxy}-pregna-5,17(20)-diene 
• 69454-82-6 3β-tert-butyldimethylsilyloxy-20(R)-hydroxy-pregna-5-ene 
• 69454-81-5 3β-tert-butyldimethylsilyloxy-20(S)-hydroxy-pregna-5-ene 
• 979-02-2 16-dehydropregnenolone acetate 
• 58701-45-4 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one 

Downstream Products

• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 

Relevant articles and documents

Short-step Stereoselective Synthesis of 2α,3α,22-Triacetoxy-23,24-dinor-5α-cholan-6-one: Key Intermediate for the Preparation of 24-Norbrassinolide, Dolicholide and Dolichosterone

A streoselective synthesis of 6-oxo-23,24-dinor-5α-cholan-2α,3α,22-triyl triacetate 9 was achieved in 44percent overall yield in nine steps starting from 3β-hydroxyandrost-5-en-17-one 8.The important features of this synthesis are the modified Wittig reaction on the 17-oxo steroid 8 and the stereospecific generation of the chiral centre at C-20 by a resin-catalysed ene reaction on (Z)-3β, p-tolylsulfonyloxypregna-5,17(20)-diene 11.

Resin catalysed ene reaction on 3β-toluene-p-sulfonoxy-(Z)-pregna-5,17(20)-diene: Synthesis of (20s)-6β-methoxy-3 α,5-cyclo-5α-pregnane-20-carboxyaldehyde

Conversion of 17-keto steroid 2 in to 17(Z) ethylidene steroid 3 was achieved in high yields using a modified procedure. Ene reaction on 4 with paraformaldehyde in presence of acetic anhydride using various cation exchange resins as catalyst afforded stereo specifically the C-22 acetate 5 in excellent yields. For the first time cation exchange resins have been used as catalysts in ene reaction. Compound 5 was converted to C-22 aldehyde 1 using simple reaction sequence.