16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-yl acetate

Base Information

• Chemical Name: 16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-yl acetate
• CAS No.: 34209-81-9
• Molecular Formula: C23H32O4
• Molecular Weight: 372.505
• European Community (EC) Number: 251-883-6
• Mol file: 34209-81-9.mol

Synonyms:34209-81-9;NSC 21455;EINECS 251-883-6;16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-yl acetate;AKOS016014970;E0015

Chemical Property of 16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-yl acetate

Chemical Property:

• Vapor Pressure: 5.5E-09mmHg at 25°C
• Melting Point: 159 °C
• Refractive Index: 1.557
• Boiling Point: 469.5 °C at 760 mmHg
• Flash Point: 202.5 °C
• PSA: 55.90000
• Density: 1.18 g/cm³
• LogP: 4.21740
• Storage Temp.: −20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 372.23005950
• Heavy Atom Count: 27
• Complexity: 741

Purity/Quality:

97% ^*data from raw suppliers

16,17-Epoxypregnenolone Acetate >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C12C(O1)CC3C2(CCC4C3CC=C5C4(CCC(C5)OC(=O)C)C)C
• Isomeric SMILES: CC(=O)[C@]12C(O1)C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)OC(=O)C)C)C

Technology Process of 16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-yl acetate

There total 11 articles about 16-alpha,17-alpha-Epoxy-20-oxopregn-5-en-3-beta-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: 82.0%

16-dehydropregnenolone acetate (979-02-2) → Acetic acid (3S,8R,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester (34209-81-9)

Guidance literature:

With potassium hydroxide; dihydrogen peroxide; In methanol; water;

Reference yield: 63.0%

3β,21-Diacetoxy-16α,17α-epoxypregn-5-en-20-one (21853-84-9) → Acetic acid 2-((3S,8S,9S,10R,13S,14S,16R,17R)-3-acetoxy-16-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester (147292-03-3) + Acetic acid (3S,8S,9S,10R,13S,14S,16R,17R)-3-acetoxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester + Acetic acid (3S,8R,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester (34209-81-9)

Guidance literature:

With aluminum amalgam; sodium hydrogencarbonate; In ethanol; for 1h; Yields of byproduct given; Ambient temperature; ultrasonic irradiation;

DOI:10.1016/S0040-4039(00)60586-5

Reference yield:

acetic anhydride (108-24-7) + 3β-hydroxy-16α,17α-epoxypregn-5-en-20-one (974-23-2) → Acetic acid (3S,8R,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester (34209-81-9)

Guidance literature:

With pyridine;

DOI:10.1021/ja01589a071

upstream raw materials:

16-dehydropregnenolone acetate

acetic anhydride

3β-hydroxy-16α,17α-epoxypregn-5-en-20-one

silver(I) acetate

Downstream raw materials:

3β-acetoxy-16α-hydroxy-pregn-5-en-20-one

16-dehydropregnenolone acetate

3β-acetoxy-17α-hydroxy-5-pregnen-20-one

Acetic acid (2S,4aR,4bS,6aS,10aS,10bR)-7-hydroxy-4a,6a,7-trimethyl-8-oxo-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11-hexadecahydro-chrysen-2-yl ester