(2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

Base Information

• Chemical Name: (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester
• CAS No.: 202473-13-0
• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.39
• Mol file: 202473-13-0.mol

Synonyms:(2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

Chemical Property of (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

There total 7 articles about (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline 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: 80.0%

(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester (159551-89-0) → (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester (202473-13-0)

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; tert-butyl alcohol;

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

Reference yield:

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3) → (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester (202473-13-0)

Guidance literature:

Multi-step reaction with 4 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: 80 percent / N-methylmorpholine-N-oxide / osmium tetroxide / 2-methyl-propan-2-ol; H₂O

With pyridine; 1-methyl-1H-imidazole; sodium tetrahydroborate; dihydrogen peroxide; 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1: Tosylation / 2: Substitution / 3: Elimination / 4: Oxidation;

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

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester (202473-13-0)

Guidance literature:

Multi-step reaction with 6 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: 80 percent / N-methylmorpholine-N-oxide / osmium tetroxide / 2-methyl-propan-2-ol; H₂O

With pyridine; 1-methyl-1H-imidazole; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; potassium carbonate; 4-methylmorpholine N-oxide; sodium iodide; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Acylation / 2: Esterification / 3: Tosylation / 4: Substitution / 5: Elimination / 6: Oxidation;

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

upstream raw materials:

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

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

benzyl chloroformate

dibenzyl (2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

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

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

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

(2S,3RS,4SR)-3,4-dihydroxyproline