(R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester

Base Information

• Chemical Name: (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester
• CAS No.: 145452-07-9
• Molecular Formula: C₂₀H₂₉NO₄
• Molecular Weight: 347.455
• Mol file: 145452-07-9.mol

Synonyms:(R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester

Chemical Property of (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-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-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester

There total 8 articles about (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester (145484-23-7) → (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester (145452-07-9)

Guidance literature:

In tetrahydrofuran; Heating;

DOI:10.1021/ja00052a093

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester (145452-07-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) aq. NaOH / 1.) ethanol, RT, 0.5 h, 2.) pentane, reflux, 48 h

2: CH₂Cl₂ / 384 h / 5 °C

3: 1.) potassium hexamethyldisilazide / 1.) THF, toluene, -78 deg C, 15 min, 2.) THF, toluene, -78 deg C, 30 min

4: 1N aq. NaOH / methanol / 16 h / Heating

5: K₂CO₃ / dimethylformamide / 1 h / 0 - 20 °C

6: 91 percent / dimedone, Pd(PPh₃)4 / tetrahydrofuran / 16 h / Ambient temperature

7: 90 percent / tetrahydrofuran / 16 h / Heating

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hexamethylsilazane; potassium carbonate; dimedone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00101a017

Reference yield:

(R)-2-Allyloxycarbonylamino-2-benzyl-5-methyl-hex-4-enoic acid (147240-35-5) → (R)-2-Benzyl-2-tert-butoxycarbonylamino-5-methyl-hex-4-enoic acid methyl ester (145452-07-9)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 1 h / 0 - 20 °C

2: 91 percent / dimedone, Pd(PPh₃)4 / tetrahydrofuran / 16 h / Ambient temperature

3: 90 percent / tetrahydrofuran / 16 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; dimedone; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00101a017

upstream raw materials:

di-tert-butyl dicarbonate

(R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester

D-(R)-phenylalanine

(2R,4R)-4-Benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-5-(3-methyl-but-2-enyl)-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-3,4'-dioxo-5'-(2-oxo-ethyl)-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-5'-(3-methyl-but-2-enyl)-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester