(2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester

Base Information

• Chemical Name: (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester
• CAS No.: 161510-63-0
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 161510-63-0.mol

Synonyms:(2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester

Chemical Property of (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester

There total 6 articles about (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl 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: 91.0%

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (124818-94-6,116246-06-1) → (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester (161510-63-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 120h;

DOI:10.1016/j.bmcl.2006.11.020

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester (161510-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / toluene / 1 h / 80 °C

2: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; 1: Wittig reaction;

DOI:10.1016/j.bmcl.2006.11.020

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → (2S,3R,4S)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2,3-epoxy-5-phenylpentanoic acid ethyl ester (161510-63-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine*SO₃; triethylamine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 20 °C

2: 89 percent / toluene / 1 h / 80 °C

3: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

With sulfur trioxide pyridine complex; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; dimethyl sulfoxide; toluene; 2: Wittig reaction;

DOI:10.1016/j.bmcl.2006.11.020

upstream raw materials:

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Boc-L-phenylalaninal

Downstream raw materials:

(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid

(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

(2R,3S,4S)-2-(benzylamino)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydoxy-5-phenylpentanoic acid ethyl ester

tert-butyl (2S,3R,4R)-4-(ethoxycarbonyl)-3-hydroxy-1-phenyl-4-(phenylamino)butan-2-ylcarbamate