methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

Base Information

• Chemical Name: methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate
• CAS No.: 478239-50-8
• Molecular Formula: C₃₁H₃₈N₂O₉
• Molecular Weight: 582.651
• Mol file: 478239-50-8.mol

Synonyms:methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

Chemical Property of methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

There total 5 articles about methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate 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: 79.0%

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-47-3) + 4-methoxyphenylboronic acid (5720-07-0) → methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-50-8)

Guidance literature:

With palladium diacetate; sodium carbonate; tris-(o-tolyl)phosphine; In 1,2-dimethoxyethane; at 80 ℃;

DOI:10.1021/ol020160a

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-50-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiBEt₃H / tetrahydrofuran / 0.67 h / -78 °C

2.1: p-TsOH / 20 °C

3.1: 1.78 g / BF₃*Et₂O / diethyl ether / 0.25 h / -40 °C

4.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

5.1: 1.95 g / DBU / CH₂Cl₂ / 8 h / 20 °C

6.1: NBS / CHCl₃ / 1.33 h / 20 °C

6.2: 53 percent / DABCO / CHCl₃ / 24 h / 20 °C

7.1: 79 percent / Pd(OAc)2; P(o-tolyl)3; Na₂CO₃ / 1,2-dimethoxy-ethane / 80 °C

With palladium diacetate; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; boron trifluoride diethyl etherate; lithium triethylborohydride; sodium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(o-tolyl)phosphine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform; water; 5.1: Horner-Emmons olefination / 7.1: Suzuki cross-coupling;

DOI:10.1021/ol020160a

Reference yield:

1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester (188200-05-7) → methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-(4-methoxy-phenyl)-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-50-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: p-TsOH / 20 °C

2.1: 1.78 g / BF₃*Et₂O / diethyl ether / 0.25 h / -40 °C

3.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

4.1: 1.95 g / DBU / CH₂Cl₂ / 8 h / 20 °C

5.1: NBS / CHCl₃ / 1.33 h / 20 °C

5.2: 53 percent / DABCO / CHCl₃ / 24 h / 20 °C

6.1: 79 percent / Pd(OAc)2; P(o-tolyl)3; Na₂CO₃ / 1,2-dimethoxy-ethane / 80 °C

With palladium diacetate; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; boron trifluoride diethyl etherate; sodium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(o-tolyl)phosphine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform; water; 4.1: Horner-Emmons olefination / 6.1: Suzuki cross-coupling;

DOI:10.1021/ol020160a

upstream raw materials:

methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

4-methoxyphenylboronic acid

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester