(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate

Base Information

• Chemical Name: (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate
• CAS No.: 815584-69-1
• Molecular Formula: C₃₁H₃₈N₂O₇
• Molecular Weight: 550.652
• Mol file: 815584-69-1.mol

Synonyms:(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate

Chemical Property of (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate

There total 8 articles about (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate 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: 77.0%

(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate (815584-68-0) + di-tert-butyl dicarbonate (24424-99-5) → (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate (815584-69-1)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1021/jo0485738

Reference yield:

(S)-2-(Benzyl-benzyloxycarbonyl-amino)-pent-4-enoic acid methyl ester → (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate (815584-69-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 0.82 g / aq. NaOH / methanol / 3 h

2: PyBOP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

3: 0.89 g / pyridine / CH₂Cl₂ / 1 h

4: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

With pyridine; dmap; sodium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo0485738

Reference yield:

Benzyl-[(S)-1-((R)-1-hydroxymethyl-allylcarbamoyl)-but-3-enyl]-carbamic acid benzyl ester → (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate (815584-69-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.89 g / pyridine / CH₂Cl₂ / 1 h

2: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

With pyridine; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0485738

upstream raw materials:

(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate

di-tert-butyl dicarbonate

L-allylglycine

methyl (S)-allylglycinate

Downstream raw materials:

(R)-tert-butyl 2-((2S,6R,Z)-6-(N-tert-butyloxycarbonyl)amino-2-(N-benzyl-N-benzyloxycarbonyl)amino-7-hydroxyhept-4-enamido)propanoate

(2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid

(2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate

(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester