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

Base Information

• Chemical Name: 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
• CAS No.: 256382-36-2
• Molecular Formula: C₃₆H₆₂O₆SSi₂
• Molecular Weight: 679.122
• Mol file: 256382-36-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 16 articles about 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 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: 92.5%

methyl 4-({2-[(1R,2R,3S,5S)-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-hydroxycyclopentyl]-ethyl}sulfanyl)butanoate (256382-20-4) → 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 (256382-36-2)

Guidance literature:

With sulfur trioxide pyridine complex; In dimethyl sulfoxide; ethyl acetate; at 10 ℃; Inert atmosphere;

DOI:10.1021/jo901497u

Reference yield: 27.0%

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 (256382-35-1) → 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 (256382-36-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); di-tert-butyl peroxide; tri-n-butyl-tin hydride; at 100 ℃;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 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 (256382-36-2)

Guidance literature:

Multi-step reaction with 5 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

4.1: 78 percent / DMAP; MsCl / CH₂Cl₂ / 3 h / 0 °C

5.1: 27 percent / Bu₃SnH; t-butyl peroxide; AIBN / 100 °C

With 1H-imidazole; dmap; Schwartz's reagent; 2,2'-azobis(isobutyronitrile); di-tert-butyl peroxide; tert.-butyl lithium; tri-n-butyl-tin hydride; methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane;

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

upstream raw materials:

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

3-(methoxymethyl)bromobenzene

tert-butyldimethylsilyl chloride

(3S)-4-(3-methoxymethylphenyl)-1-butyn-3-ol

Downstream raw materials:

Rivenprost

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

C₂₄H₃₂O₅S