(3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone

Base Information

• Chemical Name: (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone
• CAS No.: 917600-21-6
• Molecular Formula: C₃₄H₄₈O₃Si₂
• Molecular Weight: 560.924
• Mol file: 917600-21-6.mol

Synonyms:

Chemical Property of (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone

There total 6 articles about (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone 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:

(S)-1-(3-biphenyl)-2-(t-butyldimethylsilyloxy)-3-butyne (917600-20-5) + (4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol (117254-07-6) → (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone (917600-21-6)

Guidance literature:

(S)-1-(3-biphenyl)-2-(t-butyldimethylsilyloxy)-3-butyne; With n-butyllithium; In hexane; toluene; at 0 - 20 ℃; for 0.333333h;

With diethylaluminium chloride; In hexane; toluene; at 0 - 20 ℃; for 0.5h;

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol; With hydrogenchloride; ammonium chloride; more than 3 stages;

Reference yield:

1-(3-biphenyl)-3-butyn-2-ol (917600-16-9) → (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone (917600-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Lipase PS / toluene / 180 h / 37 °C

2.1: potassium carbonate / methanol / 1.5 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 0 - 20 °C

4.1: n-butyllithium / hexane; toluene / 0.33 h / 0 - 20 °C

4.2: 0.5 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; potassium carbonate; In methanol; hexane; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl 2-((1,1'-biphenyl)-3-yl)acetate (71912-70-4) → (3R,4R)-3-((S)-4-biphenyl-3-yl-(3-t-butyldimethylsilyloxy)-1-butyn-1-yl)-(4-t-butyldimethylsilyloxy)-2-methylenecyclopentanone (917600-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / hexane; toluene / 2 h / -70 °C

1.2: 6 h / -70 - 20 °C

2.1: Lipase PS / toluene / 180 h / 37 °C

3.1: potassium carbonate / methanol / 1.5 h / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 0 - 20 °C

5.1: n-butyllithium / hexane; toluene / 0.33 h / 0 - 20 °C

5.2: 0.5 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; potassium carbonate; In methanol; hexane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(S)-1-(3-biphenyl)-2-(t-butyldimethylsilyloxy)-3-butyne

(4R)-2-(N,N-diethylamino)methyl-4-(t-butyldimethylsiloxy)-cyclopent-2-en-1-ol

1-(3-biphenyl)-3-butyn-2-ol

(S)-1-(3-biphenyl)-3-butyn-2-ol

Downstream raw materials:

(2E)-17,18,19,20-tetranor-16-(3-biphenyl)-2,3,13,14-tetradehydro-PGE₁ methyl ester 11,15-bis(t-butyldimethylsilyl ether)