(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

Base Information

• Chemical Name: (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester
• CAS No.: 95863-95-9
• Molecular Formula: C₂₃H₂₄N₂O₈
• Molecular Weight: 456.452

Synonyms:

Chemical Property of (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

There total 3 articles about (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) 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:

N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) + (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (95863-88-0) → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (95863-95-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In acetonitrile; at 0 ℃; for 4h;

DOI:10.1016/S0040-4020(01)91497-8

Reference yield:

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid (95863-87-9,159247-18-4) → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (95863-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 250 mg / NaHCO₃ / H₂O / 0 deg C, 1h, RT

2: dicyclohexylcarbodiimide (DCC) / acetonitrile / 4 h / 0 °C

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water; acetonitrile;

DOI:10.1016/S0040-4020(01)91497-8

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-(3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (95863-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 250 mg / NaHCO₃ / H₂O / 0 deg C, 1h, RT

2: dicyclohexylcarbodiimide (DCC) / acetonitrile / 4 h / 0 °C

With sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In water; acetonitrile;

DOI:10.1016/S0040-4020(01)91497-8

upstream raw materials:

N-hydroxy-5-norbornene-2,3-dicarboximide

(2S,4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

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

benzyl chloroformate

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