(2S,4S)-N^α-Cbz-4-azidoproline benzyl ester

Base Information

• Chemical Name: (2S,4S)-N^α-Cbz-4-azidoproline benzyl ester
• CAS No.: 329191-55-1
• Molecular Formula: C₂₀H₂₀N₄O₄
• Molecular Weight: 380.403
• Mol file: 329191-55-1.mol

Synonyms:(2S,4S)-N^α-Cbz-4-azidoproline benzyl ester

Chemical Property of (2S,4S)-N^α-Cbz-4-azidoproline benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-N^α-Cbz-4-azidoproline benzyl ester

There total 6 articles about (2S,4S)-N^α-Cbz-4-azidoproline benzyl 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: 87.0%

(2S,4R)-Nα-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester (159551-87-8) → (2S,4S)-Nα-Cbz-4-azidoproline benzyl ester (329191-55-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 65 - 70 ℃; for 8h;

DOI:10.1021/jo005626m

Reference yield:

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3) → (2S,4S)-Nα-Cbz-4-azidoproline benzyl ester (329191-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine / 48 h / 20 °C

2: 80 percent / NaN₃ / dimethylformamide; H₂O / 48 h / 70 °C

With sodium azide; In pyridine; water; N,N-dimethyl-formamide;

DOI:10.1002/adsc.200505058

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2S,4S)-Nα-Cbz-4-azidoproline benzyl ester (329191-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

1.2: 70 percent / tetrahydrofuran / 24 h / Heating

2.1: 80 percent / pyridine / 48 h / 20 °C

3.1: 80 percent / NaN₃ / dimethylformamide; H₂O / 48 h / 70 °C

With sodium azide; triethylamine; In tetrahydrofuran; pyridine; water; N,N-dimethyl-formamide;

DOI:10.1002/adsc.200505058

upstream raw materials:

(2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

benzyl alcohol

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Downstream raw materials:

(2S,4S)-dibenzyl-4-(4-butyl-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

dibenzyl (2S,4S)-4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate

3-((3S,5S)-1,5-bis(benzyloxycarbonyl)pyrrolidin-3-yl)-1-methyl-3H-1,2,3-triazol-1-ium iodide

dibenzyl (2S,4S)-4-(1H-1,2,3-triazol-1-yl)pyrrolidine-1,2-dicarboxylate