3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid

Base Information

• Chemical Name: 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid
• CAS No.: 1759-35-9
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 1759-35-9.mol

Synonyms:(3S,3aS,5aS,6R,9aS,9bS)-Dodecahydro-3-hydroxy-3a,6-diMethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid;[3S-(3α,3aα,5aβ,6β,9aα,9bβ)]-Dodecahydro-3-hydroxy-3a,6-diMethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid;17β-Hydroxy-5-oxo-A-nor-3,5-secoandrostan-3-oic Acid;3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid;4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid

Chemical Property of 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid

Chemical Property:

• PSA: 74.60000
• LogP: 3.02380

Purity/Quality:

99% ^*data from raw suppliers

4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid is an open A-ring steroid that showed inhibitory activity on hormone binding by an extract from Nippostrongylus brasiliensis (Nematoda). It is used in the preparation on heterocyclic steroids.

Technology Process of 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid

There total 12 articles about 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid 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: 88.0%

testosterone (58-22-0) → 5-oxo-A-nor-3,5-seco-17β-hydroxy-androstan-3-oic acid (1759-35-9)

Guidance literature:

With potassium permanganate; sodium periodate; sodium carbonate; In water; tert-butyl alcohol; at 60 ℃;

DOI:10.1002/cmdc.202100052

Reference yield: 88.0%

5-oxo-17β-propionyloxy-4-nor-3,5-secoandrostan-3-oic acid (3510-18-7) → 5-oxo-A-nor-3,5-seco-17β-hydroxy-androstan-3-oic acid (1759-35-9)

Guidance literature:

With potassium hydroxide; In methanol; water; for 3h; Heating;

DOI:10.1016/S0040-4020(00)00966-2

Reference yield:

testosterone propionate (57-85-2) → 5-oxo-A-nor-3,5-seco-17β-hydroxy-androstan-3-oic acid (1759-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / ethyl acetate / -78 °C

1.2: 87 percent / H₂O₂ / H₂O / 20 °C

2.1: 88 percent / KOH / methanol; H₂O / 3 h / Heating

With potassium hydroxide; ozone; In methanol; water; ethyl acetate; 1.1: ozonolysis / 1.2: Reduction / 2.1: Hydrolysis;

DOI:10.1016/S0040-4020(00)00966-2

upstream raw materials:

testosterone

testosterone acetate

17β-Acetoxy-3,6-cyclo-A-nor-3,5-seco-6β-androstan-3,5-dion

ozone

Downstream raw materials:

methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate

4-methyltestosterone

3,3-Diphenyl-A-nor-3,5-seco-androstan-3,17β-diol

17β-Acetoxy-3,3-diphenyl-A-nor-3,5-seco-androsten-(2)