(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS No.: 122350-59-8
• Molecular Formula: C21H21 N O5
• Molecular Weight: 367.401
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20450664
• Nikkaji Number: J856.947I
• Wikidata: Q82270468
• Mol file: 122350-59-8.mol

Synonyms:122350-59-8;N-Fmoc-trans-4-Hydroxy-L-proline methyl ester;(2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-O-(9H-fluoren-9-ylmethyl) 2-O-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(9H-fluoren-9-ylMethyl) 2-Methyl ester, (2S,4R)-;N-Fmoc-trans-4-hydroxy-L-prolinemethylester;N-Fmoc-trans-4-hydroxy-L-prolinemethyl ester;SCHEMBL3793423;DTXSID20450664;AWCMBJJPVSUPSS-YJYMSZOUSA-N;AMY36704;CS-M3064;XEA35059;MFCD12545917;AKOS015850932;AKOS015896278;CS-W000250;DS-15391;HY-79123;PD196098;N-Fmoc-trans-4-Hydroxy-L-proline methylester;EN300-6967397;1-(2,4-Dichloro-benzyl)-1H-indazole-3-carboxylic acid methyl ester;1-(9H-Fluorene-9-ylmethoxycarbonyl)-4beta-hydroxy-L-proline methyl ester;(2S,4R)-1-((9H-Fluoren-9-yl)methyl)2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate;1-(9H-fluoren-9-yl)methyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;1-[(9H-Fluoren-9-yl)methyl] 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate;1,2-Pyrrolidinedicarboxylic acid,4-hydroxy-,1-(9H-fluoren-9-ylMethyl) 2-Methyl ester,(2S,4R)-

Chemical Property of (2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 539.04oC at 760 mmHg
• Flash Point: 279.801oC
• PSA: 76.07000
• Density: 1.329g/cm3
• LogP: 2.48160
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 367.14197277
• Heavy Atom Count: 27
• Complexity: 545

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-1-((9H-Fluoren-9-yl)methyl)2-methyl4-hydroxypyrrolidine-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O

Technology Process of (2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

There total 6 articles about (2S,4R)-1-((9H-Fluoren-9-yl)methyl) 2-methyl 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: 97.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate (122350-59-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 48h;

DOI:10.1021/ol701742x

Reference yield: 93.0%

C23H23NO6 → (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate (122350-59-8)

Guidance literature:

With methanol; potassium permanganate; trimethylsulphonium iodide; at 25 ℃; under 760.051 Torr; chemoselective reaction;

DOI:10.1039/d1ra03209g

Reference yield: 86.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate (122350-59-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 10h;

DOI:10.1016/j.chembiol.2018.11.001

upstream raw materials:

methanol

N-Fmoc-trans-4-Hydroxy-L-Proline

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(R)-4-hydroxy-L-proline ethyl ester

Refernces

• 1、 Rack, Johannes Gregor Matthias,Ariza, Antonio,Henfrey, Callum,Bartlett, Edward,Ahel, Ivan,Drown, Bryon S.,Shirai, Tomohiro,Hergenrother, Paul J.. "(ADP-ribosyl)hydrolases: Structural Basis for Differential Substrate Recognition and Inhibition". . p. 1533 - 1546. Retrieved 2018.
• 2、 Liu, Hongqiang,Pattabiraman, Vijaya R.,Vederas, John C.. "Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening". . p. 4211 - 4214. Retrieved 2008/03/13.