Tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate

Base Information

• Chemical Name: Tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate
• CAS No.: 406235-20-9
• Molecular Formula: C20H29NO4S
• Molecular Weight: 379.521
• DSSTox Substance ID: DTXSID401118896
• Mol file: 406235-20-9.mol

Synonyms:SCHEMBL1542228;SCHEMBL3593703;GHLYEFRQIKESDD-RDRICISKSA-N;DTXSID401118896;tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate;406235-20-9;tert-butyl (2e, 4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate;1,1-Dimethylethyl (2E,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(phenylthio)-2-pentenoate

Chemical Property of Tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 379.18172958
• Heavy Atom Count: 26
• Complexity: 485

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C=CC(CSC1=CC=CC=C1)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)/C=C/[C@H](CSC1=CC=CC=C1)NC(=O)OC(C)(C)C

Technology Process of Tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-2-enoate

There total 4 articles about Tert-butyl (2e,4r)-4-((tert-butoxycarbonyl)amino)-5-(phenylthio)pent-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: 83.0%

((R)-1-formyl-2-phenylsulfanylethyl)carbamic acid tert-butyl ester (406233-60-1) + (tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) → (E,R)-4-tert-butoxycarbonylamino-5-phenylsulfanylpent-2-enoic acid tert-butyl ester (406235-20-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jm050754u

Reference yield:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → (E,R)-4-tert-butoxycarbonylamino-5-phenylsulfanylpent-2-enoic acid tert-butyl ester (406235-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: iPr₂NH / CH₂Cl₂ / 0.33 h / 20 °C

2: 25.0 g / CH₂Cl₂ / 0.5 h / 20 °C

3: 68 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

4: 83 percent / tetrahydrofuran / 24 h / 20 °C

With diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; dichloromethane; 4: Wittig reaction;

DOI:10.1021/jm050754u

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-methanesulfonyloxypropionic acid methyl ester (187035-34-3) → (E,R)-4-tert-butoxycarbonylamino-5-phenylsulfanylpent-2-enoic acid tert-butyl ester (406235-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 25.0 g / CH₂Cl₂ / 0.5 h / 20 °C

2: 68 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

3: 83 percent / tetrahydrofuran / 24 h / 20 °C

With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; 3: Wittig reaction;

DOI:10.1021/jm050754u

upstream raw materials:

((R)-1-formyl-2-phenylsulfanylethyl)carbamic acid tert-butyl ester

(tert-Butoxycarbonylmethylene)triphenylphosphorane

N-tert-butyloxycarbonyl-L-serine methyl ester

(S)-2-tert-butoxycarbonylamino-3-methanesulfonyloxypropionic acid methyl ester