(3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide

Base Information

• Chemical Name: (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide
• CAS No.: 724733-53-3
• Molecular Formula: C₂₁H₃₂N₆O₅
• Molecular Weight: 448.522
• Mol file: 724733-53-3.mol

Synonyms:(3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide

Chemical Property of (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide

There total 8 articles about (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide 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: 63.0%

(S)-2-((S)-2-aminopropanoylamino)-4-methylpentanoic acid amide (38689-32-6) + (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid (724733-50-0) → (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide (724733-53-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1021/jm031106i

Reference yield:

H-L-Leu-NH2 (687-51-4,13079-20-4,13366-40-0,15893-47-7) → (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide (724733-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxy-7-azabenzotriazole; 1,8-bis(N,N-dimethylamino)naphthalene; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / dimethylformamide / 0 - 20 °C

2: 100 percent / H₂ / Pd/C / aq. ethanol / 1.5 h / atmospheric pressure

3: 63 percent / diisopropylethylamine; HATU / dimethylformamide / 2 h / 0 - 20 °C

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm031106i

Reference yield:

Z-(S)-Ala-(S)-Leu-NH2 (18323-56-3) → (3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid [(S)-1-((S)-1-carbamoyl-3-methylbutylcarbamoyl)ethyl]amide (724733-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / aq. ethanol / 1.5 h / atmospheric pressure

2: 63 percent / diisopropylethylamine; HATU / dimethylformamide / 2 h / 0 - 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm031106i

upstream raw materials:

(S)-2-((S)-2-aminopropanoylamino)-4-methylpentanoic acid amide

(3S,4S)-4-azido-5-benzyloxy-3-hydroxypentanoic acid

(R)-2-(benzyloxy)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

H-L-Leu-NH₂