(2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester

Base Information

• Chemical Name: (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester
• CAS No.: 202473-20-9
• Molecular Formula: C₂₀H₂₀N₄O₅
• Molecular Weight: 396.403
• Mol file: 202473-20-9.mol

Synonyms:(2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester

Chemical Property of (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester

There total 8 articles about (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline 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: 47.0%

(1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester (159651-34-0) → (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester (202473-19-6) + (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester (202473-20-9)

Guidance literature:

With sodium azide; ammonium chloride; In water; acetone; at 70 ℃; for 24h;

DOI:10.1016/S0040-4020(97)10352-0

Reference yield:

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3) → (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester (202473-20-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / N-methylimidazole / tetrahydrofuran / 0 - 30 °C

2: 74 percent / NaBH₄ / 2-methyl-propan-2-ol / 2.5 h / Heating

3: 77 percent / pyridine; H₂O₂ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4: 22 percent / m-CPBA; 4,4'-thio-(6-tert-butyl-3-methylphenol) / 1,2-dichloro-ethane / Heating

5: 23 percent / NH₄Cl; sodium azide / acetone; H₂O / 24 h / 70 °C

With pyridine; 1-methyl-1H-imidazole; sodium tetrahydroborate; sodium azide; 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox; dihydrogen peroxide; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; 1: Tosylation / 2: Substitution / 3: Elimination / 4: Epoxidation / 5: Ring cleavage;

DOI:10.1016/S0040-4020(97)10352-0

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3R,4R)-N-benzyloxycarbonyl-3-azido-4-hydroxyproline benzyl ester (202473-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / aq. NaOH / tetrahydrofuran / ice/water cooling -> room temperature

2: 71 percent / potassium carbonate; sodium iodide / dimethylformamide

3: 94 percent / N-methylimidazole / tetrahydrofuran / 0 - 30 °C

4: 74 percent / NaBH₄ / 2-methyl-propan-2-ol / 2.5 h / Heating

5: 77 percent / pyridine; H₂O₂ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

6: 22 percent / m-CPBA; 4,4'-thio-(6-tert-butyl-3-methylphenol) / 1,2-dichloro-ethane / Heating

7: 23 percent / NH₄Cl; sodium azide / acetone; H₂O / 24 h / 70 °C

With pyridine; 1-methyl-1H-imidazole; sodium hydroxide; sodium tetrahydroborate; sodium azide; 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox; dihydrogen peroxide; potassium carbonate; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Acylation / 2: Esterification / 3: Tosylation / 4: Substitution / 5: Elimination / 6: Epoxidation / 7: Ring cleavage;

DOI:10.1016/S0040-4020(97)10352-0

upstream raw materials:

(1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester

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

benzyl chloroformate

(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester