(S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid
• CAS No.: 21691-44-1
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10426353
• Nikkaji Number: J231.982I
• Wikidata: Q72516334
• Mol file: 21691-44-1.mol

Synonyms:Z-Nva-OH;21691-44-1;(S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid;Cbz-L-Norvaline;Z-L-norvaline;(2S)-2-(phenylmethoxycarbonylamino)pentanoic acid;(2S)-2-{[(benzyloxy)carbonyl]amino}pentanoic acid;N-CBZ-L-NORVALINE;(2S)-2-(((benzyloxy)carbonyl)aMino)pentanoic acid;MFCD00063167;Cbz-Nva-OH;Z-L-Nva-OH;Z-L--aminovaleric acid;benzyl-oxycarbonyl-l-norvaline;N-(Benzyloxycarbonyl)norvaline;SCHEMBL265461;n-benzyloxycarbonyl-l-norvaline;DTXSID10426353;NSJDRLWFFAWSFP-NSHDSACASA-N;AKOS015836898;AM82601;DS-16711;CS-0152583;EN300-121307;J-300354;N-alpha-BenZyloxycarbonyl-L-norvaline, (S)-N-alpha-Z-2-amino-valeric acid (CbZ-L-Nva-OH)

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid

Chemical Property:

• Vapor Pressure: 1.69E-08mmHg at 25°C
• Refractive Index: 1.533
• Boiling Point: 439.445 °C at 760 mmHg
• PKA: 4.00±0.20(Predicted)
• Flash Point: 219.568 °C
• PSA: 75.63000
• Density: 1.185 g/cm³
• LogP: 2.55700
• Storage Temp.: Store at RT.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

Z-L-norvaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CCC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid

There total 9 articles about (S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid 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: 95.0%

Cbz-D,L-norvaline-OMe (134306-33-5) → Z-L-norvaline (21691-44-1)

Guidance literature:

With subtilisin 8397; triethylamine; In carbon dioxide; at 33 - 35 ℃; for 3h; under 59280 - 60800 Torr;

DOI:10.1002/jccs.199900091

Reference yield: 77.0%

L-Norvaline (6600-40-4,498-18-0) + benzyl chloroformate (501-53-1,94274-21-2) → Z-L-norvaline (21691-44-1)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/jm00151a005

Reference yield: 70.0%

C18H30N2O3S3 + C18H29(2)HN2O3S3 + benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-(benzyloxycarbonylamino)-2-deuteropentanoic acid (950842-17-8) + Z-L-norvaline (21691-44-1)

Guidance literature:

C₁₈H₃₀N₂O₃S₃; C₁₈H₂₉⁽²⁾HN₂O₃S₃; With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃;

With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃;

benzyl chloroformate; In tetrahydrofuran; water; at 0 ℃; for 1.25h;

upstream raw materials:

L-Norvaline

benzyl chloroformate

Cbz-D,L-norvaline-OMe

(S)-(+)-methyl 2-benzyloxycarbonylaminopentanoate

Downstream raw materials:

(S)-3-[(2S,3R,4R,5S)-5-((S)-2-Benzyloxycarbonylamino-pentanoylamino)-2,3,4,6-tetrahydroxy-hexanoylamino]-3-phenyl-propionic acid benzhydryl ester

((S)-2-Benzyloxycarbonylamino-pentanoylsulfamoyl)-acetic acid ethyl ester

phosphonic acid

(S)-(+)-methyl 2-benzyloxycarbonylaminopentanoate

Refernces

• 1、 Hattori, Tetsutaro,Kitamoto, Yuichi,Maeda, Tetsuya,Miyoshi, Ikuko,Morohashi, Naoya. "Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin". . . Retrieved 2020/04/01.
• 2、 King, Amber M.,Salomé, Christophe,Dinsmore, Jason,Salomé-Grosjean, Elise,De Ryck, Marc,Kaminski, Rafal,Valade, Anne,Kohn, Harold. "Primary amino acid derivatives: Compounds with anticonvulsant and neuropathic pain protection activities". supporting information; experimental part. p. 4815 - 4830. Retrieved 2011/10/01.