4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester

Base Information

• Chemical Name: 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester
• CAS No.: 256382-34-0
• Molecular Formula: C₃₆H₆₂O₇SSi₂
• Molecular Weight: 695.121
• Mol file: 256382-34-0.mol

Synonyms:4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester

Chemical Property of 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester

There total 13 articles about 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester 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: 55.0%

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (61305-35-9) + 6-methoxycarbonyl-3-thia-hexanal (93546-02-2) + 3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene (253350-40-2) → 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester (256382-34-0)

Guidance literature:

3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene; With tert.-butyl lithium; In diethyl ether; pentane; at -70 ℃; for 1h;

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone; With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -70 ℃; for 0.5h;

6-methoxycarbonyl-3-thia-hexanal; In tetrahydrofuran; diethyl ether; pentane; at -70 ℃; for 0.5h;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester (256382-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 °C

2.1: Cp₂ZrClH / tetrahydrofuran / 0.75 h / 20 °C

2.2: 80 percent / I₂ / tetrahydrofuran / 0.25 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -70 °C

3.2: lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -70 °C

3.3: 55 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -70 °C

With 1H-imidazole; Schwartz's reagent; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

(3S)-4-(3-methoxymethylphenyl)-1-butyn-3-ol (253350-38-8) → 4-(2-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-2-hydroxy-ethylsulfanyl)-butyric acid methyl ester (256382-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 °C

2.1: Cp₂ZrClH / tetrahydrofuran / 0.75 h / 20 °C

2.2: 80 percent / I₂ / tetrahydrofuran / 0.25 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -70 °C

3.2: lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -70 °C

3.3: 55 percent / diethyl ether; pentane; tetrahydrofuran / 0.5 h / -70 °C

With 1H-imidazole; Schwartz's reagent; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0968-0896(02)00031-7

upstream raw materials:

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

6-methoxycarbonyl-3-thia-hexanal

3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene

3-(methoxymethyl)bromobenzene

Downstream raw materials:

methyl 4-({2-[(1R,2R,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]-oxy}-2-{(1E,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]oxy}-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl}-5-oxocyclopentyl]ethyl}sulfanyl)-butanoate

Rivenprost

5-thia-16-(3-methoxymethylphenyl)methylPGE₁

4-{2-[(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopent-(E)-ylidene]-ethylsulfanyl}-butyric acid methyl ester