(16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione

Base Information

• Chemical Name: (16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione
• CAS No.: 4258-83-7
• Molecular Formula: C24H30O4
• Molecular Weight: 382.5
• Mol file: 4258-83-7.mol

Synonyms:(16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione;21-Acetoxy-16α-Methylpregna-1,4,9-(11)-triene-3,20-dione

Chemical Property of (16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione

Chemical Property:

• PSA: 60.44000
• LogP: 4.20880

Purity/Quality:

98% ^*data from raw suppliers

(16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione is used in the preparation of amino steroids useful in the treatment of neurological disorders.

Technology Process of (16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione

There total 5 articles about (16α)-21-(Acetyloxy)-16-methyl-pregna-1,4,9(11)-triene-3,20-dione 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:

C27H38O4Si → 2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (4258-83-7) + C24H30O4 + C24H30O6 + C24H30O5 + C24H30O6 + 17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9)

Guidance literature:

With peracetic acid; acetic acid; In dichloromethane; at 3 - 4 ℃; for 19h; Inert atmosphere;

DOI:10.1016/j.steroids.2013.09.008

Reference yield:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5) → 2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (4258-83-7) + C24H30O4 + C24H30O6 + C24H30O5 + C24H30O6 + 17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper dichloride / tetrahydrofuran / 0.02 h / 3 °C / Inert atmosphere

1.2: 0.03 h / 3 °C / Inert atmosphere

1.3: 0.2 h / 2 °C / Inert atmosphere

2.1: peracetic acid; acetic acid / dichloromethane / 19 h / 3 - 4 °C / Inert atmosphere

With peracetic acid; acetic acid; copper dichloride; In tetrahydrofuran; dichloromethane; 1.2: |Grignard Reaction;

DOI:10.1016/j.steroids.2013.09.008

Reference yield:

prednisolon (50-24-8,8056-11-9) → 2-oxo-2-((8S,10S,13S,14S,16R,17S)-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)ethyl acetate (4258-83-7) + C24H30O4 + C24H30O6 + C24H30O5 + C24H30O6 + 17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere

1.2: 1.25 h / 5 - 20 °C

2.1: dmap / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere

4.1: copper dichloride / tetrahydrofuran / 0.02 h / 3 °C / Inert atmosphere

4.2: 0.03 h / 3 °C / Inert atmosphere

4.3: 0.2 h / 2 °C / Inert atmosphere

5.1: peracetic acid; acetic acid / dichloromethane / 19 h / 3 - 4 °C / Inert atmosphere

With peracetic acid; dmap; thionyl chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride; In tetrahydrofuran; dichloromethane; 4.2: |Grignard Reaction;

DOI:10.1016/j.steroids.2013.09.008

upstream raw materials:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

prednisolon

Refernces