(2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid

Base Information

• Chemical Name: (2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid
• CAS No.: 368449-02-9
• Molecular Formula: C₂₇H₂₅NO₄
• Molecular Weight: 427.5
• Mol file: 368449-02-9.mol

Synonyms:(2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid

Chemical Property of (2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid

There total 1 articles about (2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid 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: 66.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S,3S,4E)-3-amino-2-methyl-5-phenylpent-4-enoic acid (368449-00-7) → (2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid (368449-02-9)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; at 0 - 20 ℃; for 12h;

DOI:10.1039/b100402f

Reference yield:

(2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid (368449-02-9) → cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-α-(R)-Glu-α-OH-γ-Sar-(R)-Asp-α-OH-β-(S)-Phe-]

Guidance literature:

Multi-step reaction with 3 steps

1: 27 percent / DIPEA; BOP-Cl / CH₂Cl₂; dimethylformamide / 6 h / 0 °C

2: 80 percent / aq. LiOH / tetrahydrofuran / 1 h / 0 °C

With lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100402f

Reference yield:

(2S,3S,4E)-3-[N-(fluoren-9-ylmethoxycarbonyl)amino]-2-methyl-5-phenylpent-4-enoic acid (368449-02-9) → cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-β-(R)-Glu-α-OMe-γ-(S)-Pro-(R)-Asp-α-OMe-β-(S)-Phe-] (368449-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 23 percent / DIPEA; BOP-Cl / CH₂Cl₂; dimethylformamide / 6 h / 0 °C

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100402f

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2S,3S,4E)-3-amino-2-methyl-5-phenylpent-4-enoic acid

Downstream raw materials:

cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-α-(R)-Glu-α-OMe-γ-Sar-(R)-Asp-α-OMe-β-(S)-Phe-]

cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-β-(R)-Glu-α-OMe-γ-(S)-Pro-(R)-Asp-α-OMe-β-(S)-Phe-]