ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate

Base Information

• Chemical Name: ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate
• CAS No.: 457100-63-9
• Molecular Formula: C₃₇H₆₄O₆Si₂
• Molecular Weight: 661.083

Synonyms:ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate

Chemical Property of ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate

There total 17 articles about ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate 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:

(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-formylcyclopentane-1-N,O-dimethylhydroxamine (457100-54-8) → ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate (457100-63-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi; MgBr₂ / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C

1.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / -78 °C

2.1: (EtO)3SiH / [RuCp*(CH₃CN)3]*PF₆ / CH₂Cl₂ / 2 h / 0 - 20 °C

2.2: 92 percent / CsF / CH₂Cl₂; ethanol / 12 h / 20 °C

3.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 - 20 °C

4.1: 81 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 4 h / -78 °C

5.1: potassium hexamethyldisilazide / 1,2-dimethoxy-ethane / 1 h / -78 °C

5.2: 1,2-dimethoxy-ethane / 17 h / -78 - 20 °C

With pyridine; n-butyllithium; Triethoxysilane; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium bromide; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 5.2: Julia olefination;

DOI:10.1002/chem.200305634

Reference yield:

(3R,3aR,5S,6aS)-5-(tert-butyldimethylsilyloxy)-3-(2-naphthoxy)-hexahydrocyclopenta[c]furan-1-one (457100-53-7) → ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate (457100-63-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: i-PrMgCl / tetrahydrofuran / 0.5 h / -10 °C

1.2: 72 percent / DBU / CH₂Cl₂ / 6 h / Heating

2.1: n-BuLi; MgBr₂ / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C

2.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / -78 °C

3.1: (EtO)3SiH / [RuCp*(CH₃CN)3]*PF₆ / CH₂Cl₂ / 2 h / 0 - 20 °C

3.2: 92 percent / CsF / CH₂Cl₂; ethanol / 12 h / 20 °C

4.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 - 20 °C

5.1: 81 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 4 h / -78 °C

6.1: potassium hexamethyldisilazide / 1,2-dimethoxy-ethane / 1 h / -78 °C

6.2: 1,2-dimethoxy-ethane / 17 h / -78 - 20 °C

With pyridine; n-butyllithium; Triethoxysilane; isopropylmagnesium chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium bromide; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 6.2: Julia olefination;

DOI:10.1002/chem.200305634

Reference yield:

(3S,3aS,5R,6aR)-5-Hydroxy-3-(naphthalen-2-yloxy)-hexahydro-cyclopenta[c]furan-1-one (457100-52-6) → ethyl (E)-(R)-4-(tert-butyldimethylsilyloxy)-{(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-[(E)-(S)-6-(4-methoxyphenoxy)hept-1-enyl]cyclopentyl}but-2-enoate (457100-63-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1.96 g / pyridine / 1 h / 20 °C

2.1: i-PrMgCl / tetrahydrofuran / 0.5 h / -10 °C

2.2: 72 percent / DBU / CH₂Cl₂ / 6 h / Heating

3.1: n-BuLi; MgBr₂ / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C

3.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 4 h / -78 °C

4.1: (EtO)3SiH / [RuCp*(CH₃CN)3]*PF₆ / CH₂Cl₂ / 2 h / 0 - 20 °C

4.2: 92 percent / CsF / CH₂Cl₂; ethanol / 12 h / 20 °C

5.1: 94 percent / pyridine / CH₂Cl₂ / 1 h / 0 - 20 °C

6.1: 81 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 4 h / -78 °C

7.1: potassium hexamethyldisilazide / 1,2-dimethoxy-ethane / 1 h / -78 °C

7.2: 1,2-dimethoxy-ethane / 17 h / -78 - 20 °C

With pyridine; n-butyllithium; Triethoxysilane; isopropylmagnesium chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium bromide; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 7.2: Julia olefination;

DOI:10.1002/chem.200305634

upstream raw materials:

5-[(S)-5-(4-methoxyphenoxy)hexyl-1-sulfonyl]-1-phenyl-1H-tetrazole

(E)-(S)-[(1R,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(formyl)cyclopentyl]-4-(tert-butyldimethylsilyloxy)but-2-ynoic acid ethyl ester

t-butyldimethylsiyl triflate

(S)-5-(4-methoxyphenoxy)-hexan-1-ol

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