(2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Base Information

• Chemical Name: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester
• CAS No.: 202473-19-6
• Molecular Formula: C₂₀H₂₀N₄O₅
• Molecular Weight: 396.403
• Mol file: 202473-19-6.mol

Synonyms:(2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Chemical Property of (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

There total 15 articles about (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-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: 90.0%

(3S,4S)-4-azido-1-[(benzyloxy)carbonyl]-3-hydroxy-L-proline (1414607-55-8) + benzyl bromide (100-39-0) → (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester (202473-19-6)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1055/s-0032-1316612

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,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester (202473-19-6)

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: 47 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

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

Downstream raw materials:

(2S,3R,4S)-3-hydroxy-4-aminoproline