(2R,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

Base Information

• Chemical Name: (2R,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester
• CAS No.: 1215291-99-8
• Molecular Formula: C13H15NO5
• Molecular Weight: 265.266
• Mol file: 1215291-99-8.mol

Synonyms:trans-N-Benzyloxycarbonyl-3-hydroxyprolin;(2R,3R)-3-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester;

Chemical Property of (2R,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

Chemical Property:

• PSA: 87.07000
• LogP: 0.78090

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester

There total 1 articles about (2R,3R)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) 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: 100.0%

(2R,3R)-3-hydroxypyrrolidine-2-carboxylic acid (119677-21-3) + benzyl chloroformate (501-53-1,94274-21-2) → (3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-D-proline (1215291-99-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/jm900598m

Reference yield: 100.0%

benzyl bromide (100-39-0) + (3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-D-proline (1215291-99-8) → C20H21NO5 (1190194-16-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jm900598m

Reference yield:

triethylsilyl chloride (994-30-9) + (3R)-1-[(benzyloxy)carbonyl]-3-hydroxy-D-proline (1215291-99-8) → (3R)-1-[(benzyloxy)carbonyl]-3-[(triethylsilyl)oxy]-D-proline

Guidance literature:

With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

upstream raw materials:

(2R,3R)-3-hydroxypyrrolidine-2-carboxylic acid

benzyl chloroformate

Downstream raw materials:

C₂₀H₂₁NO₅

Refernces

• 1、 Iwashita, Masazumi,Makide, Kumiko,Nonomura, Taro,Misumi, Yoshimasa,Otani, Yuko,Ishida, Mayuko,Taguchi, Ryo,Tsujimoto, Masafumi,Aoki, Junken,Arai, Hiroyuki,Ohwada, Tomohiko. "Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative". experimental part. p. 5837 - 5863. Retrieved 2010/03/24.