3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal

Base Information

• Chemical Name: 3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal
• CAS No.: 83457-09-4
• Molecular Formula: C₃₃H₄₂O₅
• Molecular Weight: 518.693
• Mol file: 83457-09-4.mol

Synonyms:3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal

Chemical Property of 3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal

There total 1 articles about 3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde 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: 95.0%

2-(3-Bromo-2-furyl)-1,3-dioxolane (28872-85-7) + 3β-benzyloxy-5β-androst-15-en-17-one (73336-58-0) → 3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal (83457-09-4)

Guidance literature:

With n-butyllithium; In diethyl ether; benzene; at -70 ℃; for 0.5h;

DOI:10.1002/hlca.19820650712

Reference yield:

3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal (83457-09-4) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-2H-pyran-2-one (83457-16-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 4-dimethylaminopyridine / pyridine / 72 h / Ambient temperature

2: CaCO₃ / acetone; H₂O / 96 h / Heating

3: 92 percent / H₂ / 10percent Pd/CaCO₃ / ethanol / Ambient temperature

4: 1N HCl / tetrahydrofuran / 1 h

5: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

6: 90 percent / m-chloroperbenzoic acid, NaOAc / CH₂Cl₂ / 2 h / in an ice-bath

7: 90 percent / NaOAc / benzene / 1 h / Heating

8: 88 percent / SOCl₂ / pyridine / 1 h / in an ice-bath

9: 90 percent / 1N KOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

10: CrO₃/dipyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

11: Zn(BH₄)2 / diethyl ether; CH₂Cl₂ / 1 h

12: 80 percent / triethylamine / CH₂Cl₂ / 0.5 h / in an ice-bath

13: 86 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / benzene / 1 h / Heating

With chromium(VI) oxide; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; zinc(II) tetrahydroborate; dipyridine; DBN; hydrogen; sodium acetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; dmap; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; benzene;

DOI:10.1002/hlca.19820650712

Reference yield:

3-(3'β-benzyloxy-17'β-hydroxy-5'β-androst-15'-en-17'α-yl)furan-2-carbaldehyde ethylene acetal (83457-09-4) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3-oxo-3,6-dihydro-2H-pyran-6-yl acetate (86708-95-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 4-dimethylaminopyridine / pyridine / 72 h / Ambient temperature

2: CaCO₃ / acetone; H₂O / 96 h / Heating

3: 92 percent / H₂ / 10percent Pd/CaCO₃ / ethanol / Ambient temperature

4: 1N HCl / tetrahydrofuran / 1 h

5: 95 percent / NaBH₄ / tetrahydrofuran; methanol / Ambient temperature

6: 90 percent / m-chloroperbenzoic acid, NaOAc / CH₂Cl₂ / 2 h / in an ice-bath

7: 90 percent / NaOAc / benzene / 1 h / Heating

8: 88 percent / SOCl₂ / pyridine / 1 h / in an ice-bath

With hydrogenchloride; sodium tetrahydroborate; thionyl chloride; hydrogen; sodium acetate; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; dmap; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetone; benzene;

DOI:10.1002/hlca.19820650712

upstream raw materials:

2-(3-Bromo-2-furyl)-1,3-dioxolane

3β-benzyloxy-5β-androst-15-en-17-one

Downstream raw materials:

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

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

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

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-6-hydroxy-3,6-dihydro-2H-pyran-3-one