5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one

Base Information

• Chemical Name: 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one
• CAS No.: 83911-60-8
• Molecular Formula: C₃₁H₄₀O₄
• Molecular Weight: 476.656
• Mol file: 83911-60-8.mol

Synonyms:5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one

Chemical Property of 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one

There total 8 articles about 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-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:

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal (83911-56-2) → 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one (83911-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 3 N HCl / tetrahydrofuran / 5 h / Heating

2: 75 percent / Ag₂CO₃/Celite / benzene / 0.17 h / Heating

3: 1.) Et₃N; 2.) DBN / 1.) CH₂Cl₂, in ice-bath, 30 min; 2.) benzene, reflux, 1 h

4: 1.) NBS, 1percent HClO₄; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, H₂O, r. t., 30 min; 2.) MeOH, CH₂Cl₂, 30 min

With hydrogenchloride; N-Bromosuccinimide; perchloric acid; 2,6-dichloro-benzonitrile; Celite; sodium acetate; triethylamine; silver carbonate; nickel; In tetrahydrofuran; benzene;

DOI:10.1002/hlca.19830660831

Reference yield:

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)furan-2-carbaldehyde ethylene acetal (83911-55-1) → 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one (83911-60-8)

Guidance literature:

Multi-step reaction with 7 steps

1: O₂, 5,10,15,20-tetraphenylporphine / CH₂Cl₂ / 0.33 h / Irradiation

2: Me₂S / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 82 percent / NaBH₄, H₂O, 2 N KOH / tetrahydrofuran; H₂O / 4 h / Ambient temperature

4: 95 percent / 3 N HCl / tetrahydrofuran / 5 h / Heating

5: 75 percent / Ag₂CO₃/Celite / benzene / 0.17 h / Heating

6: 1.) Et₃N; 2.) DBN / 1.) CH₂Cl₂, in ice-bath, 30 min; 2.) benzene, reflux, 1 h

7: 1.) NBS, 1percent HClO₄; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, H₂O, r. t., 30 min; 2.) MeOH, CH₂Cl₂, 30 min

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; perchloric acid; dimethylsulfide; 2,6-dichloro-benzonitrile; Celite; water; oxygen; sodium acetate; 5,15,10,20-tetraphenylporphyrin; triethylamine; silver carbonate; nickel; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1002/hlca.19830660831

Reference yield:

5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3,6-dihydro-2H-pyran-2,3-diol (83911-57-3) → 5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one (83911-60-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Ag₂CO₃/Celite / benzene / 0.17 h / Heating

2: 1.) Et₃N; 2.) DBN / 1.) CH₂Cl₂, in ice-bath, 30 min; 2.) benzene, reflux, 1 h

3: 1.) NBS, 1percent HClO₄; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, H₂O, r. t., 30 min; 2.) MeOH, CH₂Cl₂, 30 min

With N-Bromosuccinimide; perchloric acid; 2,6-dichloro-benzonitrile; Celite; sodium acetate; triethylamine; silver carbonate; nickel; In benzene;

DOI:10.1002/hlca.19830660831

upstream raw materials:

2-mesitylenesulphonyl chloride

5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3,6-dihydro-2H-pyran-2,3-diol

5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3-hydroxy-3,6-dihydro-2H-pyran-2-one

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal

Downstream raw materials:

bufalin