methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

Base Information

• Chemical Name: methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate
• CAS No.: 366498-31-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 366498-31-9.mol

Synonyms:methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

Chemical Property of methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

There total 1 articles about methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate 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:

di-tert-butyl dicarbonate (24424-99-5) + methyl N-(diphenylmethylene)glycinate (81167-39-7) + (E)-cinnamyl diethyl phosphate (85669-63-2) → (E)-2-tert-Butoxycarbonylamino-5-phenyl-pent-4-enoic acid methyl ester + methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate (366498-31-9)

Guidance literature:

methyl N-(diphenylmethylene)glycinate; (E)-cinnamyl diethyl phosphate; With N,N'-((1S,2S)-cyclohexane-1,2-diyl)dipicolinamide; lithium diisopropyl amide; C₇H₈Mo(CO)3; In tetrahydrofuran; at 0 ℃;

With hydrogenchloride;

di-tert-butyl dicarbonate; With triethylamine; Further stages.;

DOI:10.1021/ja020290e

Reference yield: 70.0%

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate (366498-31-9) → (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester (366498-32-0)

Guidance literature:

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate; With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 0 - 20 ℃;

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 - 20 ℃;

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(01)00532-4

Reference yield:

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate (366498-31-9) → (3S,6S,8S,9S)-1,4-diaza-3-benzyl-9-carbomethoxy-8-phenyl-2-oxo bicyclo-[4,3,0]nonane

Guidance literature:

Multi-step reaction with 7 steps

1.1: BF₃*THF / tetrahydrofuran / 0 - 20 °C

1.2: MCPBA / tetrahydrofuran / 0 - 20 °C

1.3: 70 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 90 mg / PPTS / 24 h / 20 °C

3.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

3.2: 92 percent / BF₃*Et₂O / diethyl ether / 0.25 h

4.1: aq. HCl / 0.5 h / 20 °C

5.1: 450 mg / N-ethylmorpholine / CH₂Cl₂ / 24 h

6.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

6.2: 90 percent / Me₂S / CH₂Cl₂ / -78 - 20 °C

7.1: 80 percent / H₂ / Pd/BaSO₄ / methanol / 24 h

With N-ethylmorpholine;; hydrogenchloride; boron trifluoride-tetrahydrofuran complex; copper(I) bromide dimethylsulfide complex; hydrogen; pyridinium p-toluenesulfonate; ozone; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.3: Swern oxidation;

DOI:10.1016/S0040-4020(01)00532-4

upstream raw materials:

di-tert-butyl dicarbonate

methyl N-(diphenylmethylene)glycinate

(E)-cinnamyl diethyl phosphate

Downstream raw materials:

(3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester

(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-D-proline methyl ester

(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester