(11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one

Base Information

• Chemical Name: (11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one
• CAS No.: 56736-68-6
• Molecular Formula: C25H36O6
• Molecular Weight: 432.557
• DSSTox Substance ID: DTXSID40476947
• Wikidata: Q82308913
• Mol file: 56736-68-6.mol

Synonyms:56736-68-6;(11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one;[2-[(8S,9S,10R,11S,13S,14S,17R)-3-ethoxy-11,17-dihydroxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;SCHEMBL16407332;DTXSID40476947;(11b)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one

Chemical Property of (11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one

Chemical Property:

• PSA: 93.06000
• LogP: 3.31360
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 432.25118886
• Heavy Atom Count: 31
• Complexity: 830

Purity/Quality:

97% ^*data from raw suppliers

(11-BETA)-21-(ACETYLOXY)-3-ETHOXY-11,17-DIHYDROXY-PREGNA-3,5-DIEN-20-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC1=CC2=CCC3C4CCC(C4(CC(C3C2(CC1)C)O)C)(C(=O)COC(=O)C)O
• Isomeric SMILES: CCOC1=CC2=CC[C@H]3[C@@H]4CC[C@@]([C@]4(C[C@@H]([C@@H]3[C@]2(CC1)C)O)C)(C(=O)COC(=O)C)O
• Uses: Glucocorticoid.

Technology Process of (11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one

There total 2 articles about (11|A)-21-(Acetyloxy)-3-ethoxy-11,17-dihydroxy-pregna-3,5-dien-20-one 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: 66.0%

hydrocortisone acetate (50-03-3) + orthoformic acid triethyl ester (122-51-0) → 2-((8S,9S,10R,11S,13S,14S,17R)-3-ethoxy-11,17-dihydroxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (56736-68-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; at 20 ℃; for 4h;

Reference yield:

→ 3-Aethoxy-21-acetoxy-11β,17α-dihydroxy-pregn-3,5-dien-20-on (56736-68-6)

Guidance literature:

Acetoxy-6β,11β,17α-trihydroxy-pregn-4-en-3,20-dion, EtOH, Sonnenlicht;

DOI:10.1021/jo01283a071

Reference yield: 64.4%

2-((8S,9S,10R,11S,13S,14S,17R)-3-ethoxy-11,17-dihydroxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (56736-68-6) → RU 18748 (4004-68-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; ethyl acetate; at 20 ℃; for 0.5h; under 760.051 Torr;

upstream raw materials:

hydrocortisone acetate

orthoformic acid triethyl ester

Downstream raw materials:

RU 18748

RU 18760

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate