(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS No.: 13500-53-3
• Molecular Formula: C20H21NO5
• Molecular Weight: 355.39
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20472548
• Nikkaji Number: J2.367.376B
• Wikidata: Q82301527
• Mol file: 13500-53-3.mol

Synonyms:13500-53-3;(2S,4R)-1,2-Dicarbobenzyloxy-4-hydroxypyrrolidine;(2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate;dibenzyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;2s4r-12-dicarbobenzyloxy-4-hydroxypyrrolidine;SCHEMBL2678864;DTXSID20472548;1,2-dibenzyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;AMY36416;MFCD12407103;AKOS015836771;AKOS015896280;AS-69840;CS-0156263;C72392;?2s?4r?-1?2-dicarbobenzyloxy-4-hydroxypyrrolidine;(2S,4R)-Dibenzyl4-hydroxypyrrolidine-1,2-dicarboxylate;N-(benzyloxycarbonyl)-trans-4-hydroxy-l-proline benzyl ester;DIBENZYL (2S,4R)-4-HYDROXY-1,2-PYRROLIDINEDICARBOXYLATE;(2S,4R)-4-HYDROXY-1,2-PYRROLIDINEDICARBOXYLIC ACID 1,2-BIS(PHENYLMETHYL) ESTER;1,2-Pyrrolidinedicarboxylicacid,4-hydroxy-,1,2-bis(phenylmethyl)ester,(2S,4R)-

Chemical Property of (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Boiling Point: 517.884 °C at 760 mmHg
• Flash Point: 267.007 °C
• PSA: 76.07000
• Density: 1.3 g/cm³
• LogP: 2.43970
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 355.14197277
• Heavy Atom Count: 26
• Complexity: 471

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-1,2-Dicarbobenzyloxy-4-hydroxypyrrolidine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3)O
• Isomeric SMILES: C1[C@H](CN([C@@H]1C(=O)OCC2=CC=CC=C2)C(=O)OCC3=CC=CC=C3)O

Technology Process of (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate

There total 13 articles about (2S,4R)-Dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate 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%

benzyl bromide (100-39-0) + (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1002/adsc.200800555

Reference yield: 94.0%

benzyl chloride (100-44-7) + (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3)

Guidance literature:

With caesium carbonate; Ambient temperature;

Reference yield: 81.5%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (2S,4R)-4-hydroxyproline benzyl ester p-toluenesulfonate (88501-00-2) → N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester (13500-53-3)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 ℃;

DOI:10.1021/jo049103g

upstream raw materials:

benzyl chloride

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

benzyl bromide

N-(Benzyloxycarbonyloxy)succinimide

Downstream raw materials:

(2S,4R)-4-(formyloxy)-1,2-pyrrolidinecarboxylic acid 1,2-bis(phenylmethyl ester)

(2S,4S)-4-(formyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

(2S,4R)-4-(pivaloyloxy)-1,2-pyrrolidinedicarboxylic acid 1,2-bis(phenylmethyl ester)