(1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol

Base Information

• Chemical Name: (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol
• CAS No.: 1362209-54-8
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789
• Mol file: 1362209-54-8.mol

Synonyms:(1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol

Chemical Property of (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol

There total 9 articles about (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol 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:

(1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-iodocyclopent-2-enol (1362209-48-0) + C25H43BOSi (1362209-51-5) → (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol (1362209-54-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ol300431n

Reference yield:

(1R,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol (189104-95-8) → (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol (1362209-54-8)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; diethylazodicarboxylate / toluene / 18 h / -30 °C

2: sodium hydroxide / tetrahydrofuran; methanol; water / 0.5 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 3.5 h / 90 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: Mitsunobu reaction / 5: Suzuki-Miyaura coupling;

DOI:10.1021/ol300431n

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene (1287305-45-6) → (1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-((S)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-enol (1362209-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 4 h / 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide; In tetrahydrofuran; 2: Suzuki-Miyaura coupling;

DOI:10.1021/ol300431n

upstream raw materials:

(1R,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol

(R)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene

(1S,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol

(1S,4S)-4-((p-methoxybenzyloxy)methoxy)-3-iodocyclopent-2-enol

Downstream raw materials:

tert-butyl ((S)-2-((2R,5S,9S)-9-hydroxy-1-(2,2,2-trichloroacetyl)-1-azaspiro[4.4]non-6-en-2-yl)-1-phenylethyl)carbamate

tert-butyl ((S)-2-((2R,5S,9S)-9-(carbamoyloxy)-1-(2,2,2-trichloroacetyl)-1-azaspiro[4.4]non-6-en-2-yl)-1-phenylethyl)carbamate

tert-butyl ((S)-2-((2'S,3aS,5'R,6aS)-2-oxo-1'-(2,2,2-trichloroacetyl)-2,3,3a,6a-tetrahydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidin]-5'-yl)-1-phenylethyl)carbamate

2,6-dichloro-4-(((S)-2-((2'S,3aS,5'R,6aS)-2-oxo-1'-(2,2,2-trichloroacetyl)-2,3,3a,6a-tetrahydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidin]-5'-yl)-1-phenylethyl)carbamoyl)phenyl acetate