Z-Asp-OBzl

Base Information

• Chemical Name: Z-Asp-OBzl
• CAS No.: 4779-31-1
• Molecular Formula: C19H19NO6
• Molecular Weight: 357.363
• DSSTox Substance ID: DTXSID60426388
• Nikkaji Number: J80.901B
• Wikidata: Q72515288
• Mol file: 4779-31-1.mol

Synonyms:Z-Asp-OBzl;4779-31-1;N-Carbobenzyloxy-L-aspartic acid 1-benzyl Ester;1-Benzyl N-carbobenzyloxy-L-aspartate;(S)-4-(BENZYLOXY)-3-(((BENZYLOXY)CARBONYL)AMINO)-4-OXOBUTANOIC ACID;Z-Asp-OBn;Cbz-(L)-Asp-OBn;(3S)-4-(benzyloxy)-3-{[(benzyloxy)carbonyl]amino}-4-oxobutanoic acid;(3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoic acid;SCHEMBL4280669;DTXSID60426388;UYOZWZKJQRBZRH-INIZCTEOSA-N;Z-L-aspartic acid |A-benzyl ester;MFCD00038594;AKOS015919727;AM81614;CS-W009401;FD10540;HY-W008685;benzyloxycarbonyl-l-aspartic-benzyl ester;AS-18373;EN300-1722126;A827341;J-300062;Q-101787;N-(Benzyloxycarbonyl)-L-aspartic acid 1-benzyl ester;(s)-4-(benzyloxy)-3-(benzyloxycarbonylamino)-4-oxobutanoic acid;(S)-4-(Benzyloxy)-3-[(benzyloxycarbonyl)amino]-4-oxobutyric acid;(3S)-4-oxidanylidene-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoic acid

Chemical Property of Z-Asp-OBzl

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 1.85E-14mmHg at 25°C
• Melting Point: 83-85 °C
• Refractive Index: 1.581
• Boiling Point: 583.5 °C at 760 mmHg
• PKA: 4.09±0.19(Predicted)
• Flash Point: 306.7 °C
• PSA: 101.93000
• Density: 1.293 g/cm³
• LogP: 2.89040
• Storage Temp.: Store at RT.
• Solubility.: Acetone, Chloroform, DMSO, Ether, Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 357.12123733
• Heavy Atom Count: 26
• Complexity: 469

Purity/Quality:

min 98.0% ^*data from raw suppliers

N-Carbobenzyloxy-L-aspartic Acid 1-Benzyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CC(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CC(=O)O)NC(=O)OCC2=CC=CC=C2
• Uses: N-Carbobenzyloxy-L-aspartic Acid 1-Benzyl Ester (cas# 4779-31-1) is a compound useful in organic synthesis.

Technology Process of Z-Asp-OBzl

There total 17 articles about Z-Asp-OBzl 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: 82.0%

benzyl alcohol (100-51-6,185532-71-2) + N-benzyloxycarbonyl-L-aspartic acid anhydride (4515-23-5) → Z-Asp-OBn (4779-31-1)

Guidance literature:

at 90 ℃; for 3.5h;

Reference yield: 58.0%

3-hydroxymethylpyridin (100-55-0) + Isopropenyl chloroformate (57933-83-2) + N-Cbz-L-Asp (1152-61-0) → Z-Asp(OBzl)-OH (3479-47-8) + Z-Asp-OBn (4779-31-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h; Yield given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)95388-7

Reference yield: 58.0%

N-Cbz-L-Asp (1152-61-0) + benzyl chloroformate (501-53-1,94274-21-2) → Z-Asp(OBzl)-OH (3479-47-8) + Z-Asp-OBn (4779-31-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)95388-7

upstream raw materials:

(S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid

benzyl alcohol

N-benzyloxycarbonyl-L-aspartic acid anhydride

O¹-benzyl-N-benzyloxycarbonyl-L-aspartic acid-anhydride

Downstream raw materials:

N⁶-L-β-aspartyl-L-lysine

N-(benzyloxycarbonyl)-L-aspartic acid-4-chloride-1-benzyl ester

benzyl L-2-benzyloxycarbonylamino-5-diazo-4-oxopentanoate

N²-benzyloxycarbonyl-N⁴-octadecyl-L-asparagine benzyl ester

Refernces

• 1、 Wiemann, Arndt,Frank, Ronald,Tegge, Werner. "Synthesis of suitably protected hydroxymethylene phosphonate- and 'phosphate phosphonate'-analogues of phosphoserine and their incorporation into synthetic peptides". . p. 1331 - 1337. Retrieved 2007/10/03.
• 2、 Burtin, Guillaume,Corringer, Pierre-Jean,Hitchcock, Peter B.,Young, Douglas W.. "Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones". . p. 4275 - 4278. Retrieved 2007/10/03.