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

Base Information

• Chemical Name: 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal
• CAS No.: 83911-56-2
• Molecular Formula: C₃₃H₄₆O₅
• Molecular Weight: 522.725
• Mol file: 83911-56-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal 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: 82.0%

(Z)-2-((3S,5R,8R,9S,10S,13R,17S)-3-Benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-4-[1,3]dioxolan-2-yl-4-oxo-but-2-enal → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal (83911-56-2)

Guidance literature:

With potassium hydroxide; sodium tetrahydroborate; water; In tetrahydrofuran; water; for 4h; Ambient temperature;

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) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal (83911-56-2)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; oxygen; 5,15,10,20-tetraphenylporphyrin; Yield given. Multistep reaction; 1.) CH₂Cl₂, irradiated, -70 deg C, 2.) water, tetrahydrofuran;

DOI:10.1139/v82-309

Reference yield:

4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)furan-2-carbaldehyde ethylene acetal (84693-13-0) → 4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)2,5-dihydroxy-3-pentanal ethylene acetal (83911-56-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / SOCl₂ / pyridine / 1.) 30 min, ice-bath; 2.) 30 min, r. t.

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

3: Me₂S / CH₂Cl₂ / 0.75 h / Ambient temperature

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

With potassium hydroxide; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; water; oxygen; 5,15,10,20-tetraphenylporphyrin; In tetrahydrofuran; pyridine; dichloromethane; water;

DOI:10.1002/hlca.19830660831

upstream raw materials:

4-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)furan-2-carbaldehyde ethylene acetal

4-(3'β-benzyloxy-15'β-hydroxy-5'β-androstan-17'β-yl)furan-2-carbaldehyde ethylene acetal

4-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-Bis-benzyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-furan-2-carbaldehyde

Downstream raw materials:

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

bufalin

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

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