(2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Base Information

• Chemical Name: (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS No.: 146499-25-4
• Molecular Formula: C₂₁H₂₁NO₇
• Molecular Weight: 399.4
• Mol file: 146499-25-4.mol

Synonyms:(2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property of (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

There total 10 articles about (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-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: 81.0%

(2S,4S,5R)-5-Benzoyloxymethyl-4-benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (146499-24-3) → (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (146499-25-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)74771-X

Reference yield:

((2R,3S,5S)-3-Benzyloxy-5-vinyl-pyrrolidin-2-yl)-methanol (146499-27-6) → (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (146499-25-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / NaHCO₃ / H₂O; CH₂Cl₂

2: 97 percent / pyridine / tetrahydrofuran

3: 1) O₃, 2) Me₂S

4: 80 percent / KMnO₄ / 2-methyl-propan-2-ol

5: 81 percent / H₂ / Pd/C

With pyridine; potassium permanganate; dimethylsulfide; hydrogen; sodium hydrogencarbonate; ozone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74771-X

Reference yield:

(5S,7S,7aR)-7-Hydroxy-5-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one (146499-26-5) → (2S,4S,5R)-5-Benzoyloxymethyl-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (146499-25-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / NaH

2: 100 percent / 1N KOH / methanol / Heating

3: 90 percent / NaHCO₃ / H₂O; CH₂Cl₂

4: 97 percent / pyridine / tetrahydrofuran

5: 1) O₃, 2) Me₂S

6: 80 percent / KMnO₄ / 2-methyl-propan-2-ol

7: 81 percent / H₂ / Pd/C

With pyridine; potassium hydroxide; potassium permanganate; dimethylsulfide; hydrogen; sodium hydride; sodium hydrogencarbonate; ozone; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74771-X

upstream raw materials:

(2S,4S,5R)-5-Benzoyloxymethyl-4-benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(5S,7S,7aR)-7-Hydroxy-5-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

((2R,3S,5S)-3-Benzyloxy-5-vinyl-pyrrolidin-2-yl)-methanol

(5S,7S,7aR)-7-Benzyloxy-5-vinyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one

Downstream raw materials:

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid