(R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester

Base Information

• Chemical Name: (R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester
• CAS No.: 198622-39-8
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.418
• Mol file: 198622-39-8.mol

Synonyms:(R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester

Chemical Property of (R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester

There total 1 articles about (R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic 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:

methanol (67-56-1) + Cbz-D-Phe (2448-45-5) + allyl bromide (106-95-6) → (R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester (198622-39-8)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0960-894X(97)00446-0

Reference yield:

(R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester (198622-39-8) → 2-((S)-3-Amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-N-((S)-1-carbamimidoyl-2-hydroxy-piperidin-3-yl)-acetamide; compound with trifluoro-acetic acid

Guidance literature:

Multi-step reaction with 6 steps

1: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) -78 deg C -> room temperature

2: Et₃N, Na(OAc)3BH / 1,2-dichloro-ethane / 8 h / 0 - 20 °C

3: 1,2-dichloro-ethane / 10 h / Heating

4: 94 percent / TFA / CH₂Cl₂ / 0 - 20 °C

5: 45 percent / EDC, HOBt, DIPEA / acetonitrile / Ambient temperature

6: 1) H₂, 2) HCl / 1) Pd/C / 1) EtOH, AcOH, H₂O, 55 psi, 2) H₂O, room temperature, 3 h

With hydrogenchloride; hydrogen; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0960-894X(97)00446-0

Reference yield:

(R)-2-Benzyl-2-benzyloxycarbonylamino-pent-4-enoic acid methyl ester (198622-39-8) → ((S)-3-Benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-acetic acid

Guidance literature:

Multi-step reaction with 4 steps

1: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) -78 deg C -> room temperature

2: Et₃N, Na(OAc)3BH / 1,2-dichloro-ethane / 8 h / 0 - 20 °C

3: 1,2-dichloro-ethane / 10 h / Heating

4: 94 percent / TFA / CH₂Cl₂ / 0 - 20 °C

With sodium tris(acetoxy)borohydride; ozone; triethylamine; triphenylphosphine; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/S0960-894X(97)00446-0

upstream raw materials:

methanol

Cbz-D-Phe

allyl bromide

Downstream raw materials:

((S)-3-Benzyl-3-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl)-acetic acid tert-butyl ester

(S)-2-Benzyl-2-benzyloxycarbonylamino-4-(tert-butoxycarbonylmethyl-amino)-butyric acid methyl ester

C₂₉H₃₇N₇O₇