N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide

Base Information

• Chemical Name: N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide
• CAS No.: 1362209-61-7
• Molecular Formula: C₂₇H₃₂Cl₃NO₅
• Molecular Weight: 556.914
• Mol file: 1362209-61-7.mol

Synonyms:N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide

Chemical Property of N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide

There total 13 articles about N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide 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%

N-((1S,5S)-5-((4-methoxybenzyloxy)methoxy)-1-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide (1362209-58-2) → N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide (1362209-61-7)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/ol300431n

Reference yield:

(1R,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol (189104-95-8) → N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide (1362209-61-7)

Guidance literature:

Multi-step reaction with 8 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

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -30 - -10 °C

7: potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 0.33 h / 170 °C

8: pyridine hydrogenfluoride / acetonitrile / 1 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tetrabutyl ammonium fluoride; potassium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Suzuki-Miyaura coupling / 7: Overman rearrangement;

DOI:10.1021/ol300431n

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene (1287305-45-6) → N-((1S,5S)-5-((p-methoxybenzyloxy)methoxy)-1-((R)-3-hydroxy-5-phenylpentyl)cyclopent-2-en-1-yl)-2,2,2-trichloroacetamide (1362209-61-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 4 h / 20 °C

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

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -30 - -10 °C

4: potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 0.33 h / 170 °C

5: pyridine hydrogenfluoride / acetonitrile / 1 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; acetonitrile; 2: Suzuki-Miyaura coupling / 4: Overman rearrangement;

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

Refernces