5-Bromo-6,19-epoxyandrostane-3,17-diol

Base Information

• Chemical Name: 5-Bromo-6,19-epoxyandrostane-3,17-diol
• CAS No.: 7745-18-8
• Molecular Formula: C₁₉H₂₉BrO₃
• Molecular Weight: 385.341
• NSC Number: 85413
• DSSTox Substance ID: DTXSID80998658
• Wikidata: Q82991352
• Mol file: 7745-18-8.mol

Synonyms:7745-18-8;NSC85413;SCHEMBL11538066;DTXSID80998658;NSC-85413;5-Bromo-6,19-epoxyandrostane-3,17-diol

Chemical Property of 5-Bromo-6,19-epoxyandrostane-3,17-diol

Chemical Property:

• Vapor Pressure: 5.07E-12mmHg at 25°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 384.13001
• Heavy Atom Count: 23
• Complexity: 527

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CC4C5(C3(CCC(C5)O)CO4)Br
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)C[C@@H]4[C@@]5([C@@]3(CC[C@@H](C5)O)CO4)Br

Technology Process of 5-Bromo-6,19-epoxyandrostane-3,17-diol

There total 9 articles about 5-Bromo-6,19-epoxyandrostane-3,17-diol 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: 77.0%

5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3,17-diacetate (2774-02-9) → 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol (7745-18-8) + 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 17-acetate (96172-02-0)

Guidance literature:

With methanol; potassium carbonate; for 2.5h; Ambient temperature;

DOI:10.1007/BF00630434

Reference yield:

5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3-acetate 17-benzoate (20154-99-8) → 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol (7745-18-8) + 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 17-benzoate (20155-01-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 16 ℃; for 1.5h;

DOI:10.1135/cccc19822423

Reference yield:

5-androstenediol (521-17-5,1963-03-7,4593-57-1,4593-58-2,14504-94-0,16895-59-3,47122-33-8,64162-67-0,75767-22-5,139973-51-6,151284-19-4) → 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol (7745-18-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 72 h / Ambient temperature

2: 64 percent / N-bromoacetamide, 70percent perchloric acid, water / dioxane / 0.5 h / Ambient temperature

3: 91 percent / lead tetraacetate, iodine / benzene / 0.83 h / Heating; Irradiation

4: 21 percent / K₂CO₃, methanol / 2.5 h / Ambient temperature

With pyridine; lead(IV) acetate; methanol; perchloric acid; water; iodine; potassium carbonate; N-bromoacetamide; In 1,4-dioxane; benzene;

DOI:10.1007/BF00630434

upstream raw materials:

5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3,17-diacetate

5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3-acetate 17-benzoate

5-androstenediol

androstenediol-3,17-diacetate

Downstream raw materials:

19-hydroxy-4-androstene-3,17-dione

Refernces

• 1、 Joska,Fajkos. "Synthesis of 19-hydroxylated analogues of androstenedione and testosterone with the cyclopropane ring in 4,5-position". . p. 2423 - 2423. Retrieved 2007/10/02.