ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

Base Information

• Chemical Name: ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate
• CAS No.: 287728-22-7
• Molecular Formula: C₃₈H₄₁NO₄SSi
• Molecular Weight: 635.899
• Mol file: 287728-22-7.mol

Synonyms:ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

Chemical Property of ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

There total 8 articles about ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-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: 97.0%

thiophenol (108-98-5) + ethyl (2E,4S)-6-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate (287728-34-1) → ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate (287728-22-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1039/b303031h

Reference yield:

(S)-4-phthalimido-1,2-butanediol (287728-31-8) → ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate (287728-22-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2.1: imidazole / CH₂Cl₂; dimethylformamide / 20 °C

2.2: 89 percent / aq. HF / acetonitrile / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: 5.78 g / CH₂Cl₂ / 20 °C

5.1: 92 percent / NaBH₄ / methanol; tetrahydrofuran / -20 °C

6.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1039/b303031h

Reference yield:

(S)-4-phthalimido-2-(tert-butyldiphenylsilyl)oxy-1-butanal (618388-42-4) → ethyl (2E,4S)-6-(1,3-dihydro-3-phenylsulfanyl-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate (287728-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 5.78 g / CH₂Cl₂ / 20 °C

2: 92 percent / NaBH₄ / methanol; tetrahydrofuran / -20 °C

3: 97 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b303031h

upstream raw materials:

thiophenol

ethyl (2E,4S)-6-(1,3-dihydro-3-hydroxy-1-oxoisoindol-2-yl)-4-(tert-butyldiphenylsilyl)oxyhex-2-enoate

(S)-4-phthalimido-1,2-butanediol

(S)-2,2-dimethyl-4-(2-phthalimidoethyl)-1,3-dioxolane

Downstream raw materials:

(1R,2S,10bR)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

(1S,2S,10bS)-1,2,3,10b-tetrahydro-1-ethoxycarbonylmethyl-10b-phenylsulfanyl-2-(tert-butyldiphenylsilyl)oxypyrido[2,1-a]isoindol-6(4H)-one

[2-(tert-butyl-diphenyl-silanyloxy)-6-oxo-1,2,3,4,6,10b-hexahydro-pyrido[2,1-a]isoindol-1-yl]-acetic acid ethyl ester