ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate

Base Information

• Chemical Name: ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate
• CAS No.: 4526-93-6
• Molecular Formula: C15H20 N2 O6
• Molecular Weight: 324.334
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30365497
• Wikidata: Q82150223
• Mol file: 4526-93-6.mol

Synonyms:Z-L-seryl-L-glycine ethyl ester;4526-93-6;ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate;AC1LZCVJ;DTXSID30365497;AKOS030240635

Chemical Property of ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate

Chemical Property:

• PSA: 113.96000
• LogP: 0.73480
• Storage Temp.: -15°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 324.13213636
• Heavy Atom Count: 23
• Complexity: 395

Purity/Quality:

99% ^*data from raw suppliers

Z-L-seryl-L-glycine ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CNC(=O)C(CO)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CCOC(=O)CNC(=O)[C@@H](CO)NC(=O)OCC1=CC=CC=C1

Technology Process of ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate

There total 13 articles about ethyl 2-[[(2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate 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: 80.7%

Z-Ser(t-Bu)-Gly-OEt (1676-76-2) → N-(N-benzyloxycarbonyl-L-seryl)-glycine ethyl ester (4526-93-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00008a005

Reference yield: 53.0%

Z-Ser-OMpt (81187-75-9) + GlyOEt*HCl (459-73-4) → N-(N-benzyloxycarbonyl-L-seryl)-glycine ethyl ester (4526-93-6)

Guidance literature:

Ambient temperature;

DOI:10.1246/cl.1982.45

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + GlyOEt*HCl (459-73-4) → N-(N-benzyloxycarbonyl-L-seryl)-glycine ethyl ester (4526-93-6)

Guidance literature:

With tetrahydrofuran; dicyclohexyl-carbodiimide;

DOI:10.1021/ja01609a099

upstream raw materials:

benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate

N-(benzyloxycarbonyl)-L-serine

GlyOEt*HCl

glycine ethyl ester hydrochloride

Downstream raw materials:

Benzyloxycarbonyl-dehydroalanyl-glycin

L-Ser-Gly

N-benzyloxycarbonyl-L-seryl=>glycyl=>-L-glutamic acid diethyl ester

N-benzyloxycarbonyl-N'-ethoxycarbonylmethyloxamide

Refernces

• 1、 Carpino, Louis A.,Mansour, El-Sayed M. E.,Sadat-Aalaee, Dean. "tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis". . p. 2611 - 2614. Retrieved 2007/10/02.
• 2、 Fahrni,Lienhard,Neuenschwander. "Peptide synthesis using 1-(4-chlorophenyl)-3-(4′-methyl-1′-piperazinyl)-2-propyn-1-one as reagent: Benzyloxycarbonyl-L-alanyl-L-cysteine methyl ester and benzyloxycarbonyl-L-aspartyl-(tert-butyl ester)-L-phenylalanyl-L-valine methyl ester". . p. 175 - 175. Retrieved 2017/05/30.