3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(acetate)

Base Information

• Chemical Name: 3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(acetate)
• CAS No.: 3517-33-7
• Molecular Formula: C27H38 O7
• Molecular Weight: 474.595
• European Community (EC) Number: 222-523-5
• DSSTox Substance ID: DTXSID20956611
• Nikkaji Number: J22.709I
• Wikidata: Q82936702
• Mol file: 3517-33-7.mol

Synonyms:EINECS 222-523-5;3517-33-7;3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(acetate);C27H38O7;DTXSID20956611;20-oxopregn-5-ene-3,17,21-triyl triacetate;3beta,17alpha,21-Triacetoxypregn-5-en-20-one

Chemical Property of 3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(acetate)

Chemical Property:

• Boiling Point: 547.7°Cat760mmHg
• Flash Point: 231.4°C
• PSA: 95.97000
• Density: 1.19g/cm³
• LogP: 4.31500
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 474.26175355
• Heavy Atom Count: 34
• Complexity: 922

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)C)C)C)OC(=O)C
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)C)C)C)OC(=O)C

Technology Process of 3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(acetate)

There total 12 articles about 3beta,17,21-Trihydroxypregn-5-en-20-one 3,17,21-tri(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:

3β-acetoxy-17α-hydroxy-5-pregnen-20-one (1863-39-4) → 3β,17,21-triacetoxy-pregn-5-en-20-one (3517-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / nachfolgende Umsetzung mit NaI und mit Kaliumacetat

2: toluene-4-sulfonic acid

With bromine; toluene-4-sulfonic acid;

DOI:10.1021/ja01585a031

Reference yield:

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) → 3β,17,21-triacetoxy-pregn-5-en-20-one (3517-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: HBr; acetic acid / Hydrieren des Reaktionsprodukts an Palladium/CaCO₃ in Aethanol

2: bromine / nachfolgende Umsetzung mit NaI und mit Kaliumacetat

3: toluene-4-sulfonic acid

With hydrogen bromide; bromine; toluene-4-sulfonic acid; acetic acid;

DOI:10.1021/ja01585a031

Reference yield:

3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate (1474-10-8) + acetic anhydride (108-24-7) → 3β,17,21-triacetoxy-pregn-5-en-20-one (3517-33-7)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1021/ja01580a051

upstream raw materials:

3β,17-diacetoxy-21-iodo-pregn-5-en-20-one

silver(I) acetate

3β,17α,21-trihydroxypregn-5-en-20-one 21-acetate

acetic anhydride

Refernces