methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate

Base Information

• Chemical Name: methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate
• CAS No.: 261509-63-1
• Molecular Formula: C₃₂H₃₁N₂O₄P
• Molecular Weight: 538.583
• Mol file: 261509-63-1.mol

Synonyms:methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate

Chemical Property of methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate

There total 5 articles about methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-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: 93.0%

triphenylphosphine (603-35-0) + methyl (Z)-2-(N-Cbz)amino-5-azidopent-2-enoate (261509-62-0) → methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate (261509-63-1)

Guidance literature:

In benzene; at 20 ℃; for 4h;

DOI:10.1055/s-2000-6219

Reference yield:

Cbz-ΔGlu-OMe (130680-59-0) → methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate (261509-63-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / NaBH₄/BF₃*OEt₂ / tetrahydrofuran / 0.05 h / -10 °C

2: 74 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

3: 44 percent / NaN₃, 15-crown-5 / dimethylformamide / 2 h / 50 °C

4: 93 percent / benzene / 4 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; 15-crown-5; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Substitution / 3: Substitution / 4: Substitution;

DOI:10.1055/s-2000-6219

Reference yield:

methyl (Z)-2-(N-Cbz)amino-5-hydroxypent-2-enoate (139125-35-2) → methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate (261509-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / pyridine / CH₂Cl₂ / 6 h / 20 °C

2: 44 percent / NaN₃, 15-crown-5 / dimethylformamide / 2 h / 50 °C

3: 93 percent / benzene / 4 h / 20 °C

With pyridine; sodium azide; 15-crown-5; In dichloromethane; N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Substitution / 3: Substitution;

DOI:10.1055/s-2000-6219

upstream raw materials:

triphenylphosphine

methyl (Z)-2-(N-Cbz)amino-5-azidopent-2-enoate

Cbz-ΔGlu-OMe

methyl (Z)-2-(N-Cbz)amino-5-hydroxypent-2-enoate

Downstream raw materials:

Boc-1-Tyr(MOM)-(Z)-ΔArg(Boc2)-OMe

Boc-1-Tyr(MOM)-(Z)-ΔOrn(Cbz)-OMe

Cbz-(Z)-Δ-Orn(Cbz)-OMe

Cbz-(Z)-ΔOrn(Cbz)-OH