4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal

Base Information

• Chemical Name: 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal
• CAS No.: 367951-88-0
• Molecular Formula: C₃₂H₄₀O₅
• Molecular Weight: 504.667
• Mol file: 367951-88-0.mol

Synonyms:4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal

Chemical Property of 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal

There total 11 articles about 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal 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: 54.0%

4-(3'α-benzyloxy-17'-acetyloxy-5'β-estr-15'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal (876017-53-7) → 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal (367951-88-0)

Guidance literature:

With water; calcium carbonate; In acetone; for 72h; Heating;

DOI:10.1021/jm0505819

Reference yield:

3-oxo-5β-estrane-17-ethylene ketal (876017-48-0) → 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal (367951-88-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 3.0 g / NaBH₄ / methanol; tetrahydrofuran / 20 °C

2.1: 78 percent / NaH / toluene / 6 h / Heating

3.1: pyridinium tribromide / tetrahydrofuran / 20 h / 4 °C

4.1: t-BuOK / benzene; dimethylsulfoxide / 20 h / 60 °C

5.1: 3.4 g / pyridinium p-toluenesulfonate; H₂O / acetone

6.1: n-BuLi / tetrahydrofuran / 0.5 h / -70 °C

6.2: 40 percent / tetrahydrofuran / 1 h / -70 °C

7.1: 96 percent / pyridine; dimethylaminopyridine / 20 °C

8.1: 54 percent / CaCO₃; H₂O / acetone / 72 h / Heating

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; water; pyridinium p-toluenesulfonate; sodium hydride; pyridinium hydrobromide perbromide; calcium carbonate; In tetrahydrofuran; methanol; dimethyl sulfoxide; acetone; toluene; benzene;

DOI:10.1021/jm0505819

Reference yield:

3α-benzyloxy-5β-estr-15-en-17-one (367951-85-7) → 4-(3'α-benzyloxy-15'β-hydroxy-5'β-estr-16'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal (367951-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -70 °C

1.2: 40 percent / tetrahydrofuran / 1 h / -70 °C

2.1: 96 percent / pyridine; dimethylaminopyridine / 20 °C

3.1: 54 percent / CaCO₃; H₂O / acetone / 72 h / Heating

With pyridine; dmap; n-butyllithium; water; calcium carbonate; In tetrahydrofuran; acetone;

DOI:10.1021/jm0505819

upstream raw materials:

4-(3'α-benzyloxy-17'-acetyloxy-5'β-estr-15'-en-17'-yl)furan-2-carboxyaldehyde ethylene acetal

3-oxo-5β-estrane-17-ethylene ketal

3α-benzyloxy-5β-estr-15-en-17-one

3α-hydroxy-5β-estrane-17-ethylene ketal

Downstream raw materials:

4-(3'α-benzyloxy-15'β-hydroxy-5'β-estran-17'β-yl)furan-2-carboxyaldehyde ethylene acetal

4-(3'α-benzyloxy-15'β-hydroxy-5'β-estran-17'β-yl)furan-2-carboxyaldehyde