19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate

Base Information

• Chemical Name: 19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate
• CAS No.: 21072-69-5
• Molecular Formula: C36H54O5S
• Molecular Weight: 598.876
• NSC Number: 174354
• DSSTox Substance ID: DTXSID40943381
• Mol file: 21072-69-5.mol

Synonyms:21072-69-5;NSC174354;19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate;NSC 174354;Cholest-5-ene-3.beta.,19-diol, 3-acetate p-toluenesulfonate;DTXSID40943381;Cholest-5-ene-3,19-diol, 3-acetate 19-(4-methylbenzenesulfonate), (3.beta.)-;NSC-174354;Cholest-5-ene-3.beta., 3-acetate p-toluenesulfonate;19-[(4-Methylbenzene-1-sulfonyl)oxy]cholest-5-en-3-yl acetate;Cholest-5-ene-3, 3-acetate 19-(4-methylbenzenesulfonate), (3.beta.)-;[17-(1,5-dimethylhexyl)-13-methyl-10-(p-tolylsulfonyloxymethyl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

Chemical Property of 19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate

Chemical Property:

• Vapor Pressure: 2.72E-17mmHg at 25°C
• Boiling Point: 660°Cat760mmHg
• Flash Point: 352.9°C
• PSA: 78.05000
• Density: 1.13g/cm³
• LogP: 9.73430
• XLogP3: 9.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 598.36919599
• Heavy Atom Count: 42
• Complexity: 1080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC23CCC(CC2=CCC4C3CCC5(C4CCC5C(C)CCCC(C)C)C)OC(=O)C

Technology Process of 19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate

There total 3 articles about 19-(((4-Methylphenyl)sulfonyl)oxy)cholest-5-en-3-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

3β-acetoxycholest-5-en-19-ol (750-59-4) + p-toluenesulfonyl chloride (98-59-9) → (3S,8S,9S,10S,13R,14S,17R)-13-methyl-17-((R)-6-methylheptan-2-yl)-10-((tosyloxy)methyl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (21072-69-5)

Guidance literature:

With dmap; In dichloromethane; for 72h;

Reference yield:

Cholesteryl acetate (604-35-3) → (3S,8S,9S,10S,13R,14S,17R)-13-methyl-17-((R)-6-methylheptan-2-yl)-10-((tosyloxy)methyl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (21072-69-5)

Guidance literature:

Multi-step reaction with 4 steps

1: perchloric acid; N-bromoacetamide / 1,4-dioxane; water / 0.75 h / 20 °C / Cooling with ice; Darkness

2: lead(IV) tetraacetate; iodine / cyclohexane / 2 h / 82 °C

3: acetic acid; zinc / water / 45 °C

4: dmap / dichloromethane / 72 h

With dmap; perchloric acid; iodine; lead(IV) tetraacetate; acetic acid; zinc; N-bromoacetamide; In 1,4-dioxane; dichloromethane; cyclohexane; water;

Reference yield:

cholesterol (57-88-5) → (3S,8S,9S,10S,13R,14S,17R)-13-methyl-17-((R)-6-methylheptan-2-yl)-10-((tosyloxy)methyl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (21072-69-5)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / dichloromethane / 10 h

2: perchloric acid; N-bromoacetamide / 1,4-dioxane; water / 0.75 h / 20 °C / Cooling with ice; Darkness

3: lead(IV) tetraacetate; iodine / cyclohexane / 2 h / 82 °C

4: acetic acid; zinc / water / 45 °C

5: dmap / dichloromethane / 72 h

With pyridine; dmap; perchloric acid; iodine; lead(IV) tetraacetate; acetic acid; zinc; N-bromoacetamide; In 1,4-dioxane; dichloromethane; cyclohexane; water;

upstream raw materials:

Cholesteryl acetate

cholesterol

3β-acetoxycholest-5-en-19-ol

p-toluenesulfonyl chloride

Downstream raw materials:

6β-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate

5-chloro-6β-nitro-5α-cholestane-3β,19-diol 3-acetate 19-tosylate