2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one

Base Information

• Chemical Name: 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one
• CAS No.: 116202-23-4
• Molecular Formula: C₃₃H₄₂O₅
• Molecular Weight: 518.693
• Mol file: 116202-23-4.mol

Synonyms:2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one

Chemical Property of 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one

There total 8 articles about 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-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: 68.0%

4-methoxy-3-buten-2-one (4652-27-1) + 3β-benzyloxy-15β-acetoxy-5β-androsttan-17β-carbonyl imidazole (116202-22-3) → 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one (116202-23-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1h; -78 deg C to room temperature;

DOI:10.1016/S0040-4020(01)85089-4

Reference yield:

3β-benzyloxy-5β-androst-15-en-17-one (73336-58-0) → 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one (116202-23-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) BuLi / 1.) hexane, ether, 0 deg C, 3h; 2.) benzene, ether, 0 deg C, 40 min.

2: DMAP / pyridine / 36 h / Ambient temperature

3: 14 g / CaCO₃ / acetone; H₂O / 42 h / Heating

4: 9.54 g / H₂, aq. NaOAc / Pd/CaCO₃ / ethanol / 2 h

5: 99 percent / DMAP / pyridine / 24 h / Ambient temperature

6: 1.) NaOAC, 18-crown-6, 2.) NaIO₄, KMnO₄, K₂CO₃ / 1.) dioxane, water, 2.) water

7: 98 percent / CHCl₃ / 40 - 50 °C

8: 68 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / -78 deg C to room temperature

With dmap; potassium permanganate; sodium periodate; n-butyllithium; 18-crown-6 ether; potassium tert-butylate; hydrogen; sodium acetate; potassium carbonate; calcium carbonate; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethanol; chloroform; water; acetone;

DOI:10.1016/S0040-4020(01)85089-4

Reference yield:

2-(3'β-benzyloxy-15'β-hydroxy-5'β-androst-16'-en-17'-yl)furan (116202-19-8) → 2-(3'β-benzyloxy-15'β-acetoxy-5'β-androsttan-17'β-yl)-4H-pyran-4-one (116202-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 9.54 g / H₂, aq. NaOAc / Pd/CaCO₃ / ethanol / 2 h

2: 99 percent / DMAP / pyridine / 24 h / Ambient temperature

3: 1.) NaOAC, 18-crown-6, 2.) NaIO₄, KMnO₄, K₂CO₃ / 1.) dioxane, water, 2.) water

4: 98 percent / CHCl₃ / 40 - 50 °C

5: 68 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / -78 deg C to room temperature

With dmap; potassium permanganate; sodium periodate; 18-crown-6 ether; potassium tert-butylate; hydrogen; sodium acetate; potassium carbonate; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethanol; chloroform;

DOI:10.1016/S0040-4020(01)85089-4

upstream raw materials:

4-methoxy-3-buten-2-one

3β-benzyloxy-15β-acetoxy-5β-androsttan-17β-carbonyl imidazole

3β-benzyloxy-5β-androst-15-en-17-one

2-(3'β-benzyloxy-15'β-hydroxy-5'β-androsttan-17β'-yl)furan

Downstream raw materials:

2-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-4H-pyran-4-one

2-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)-4H-pyran-4-one

2-(3'β-benzyloxy-14'-hydroxy-5'β,14β-androstan-17'β-yl)-4H-pyran-4-one