5241-60-1

Basic information

• Product Name: CBZ-ASP(OBZL)-OBZL
• Synonyms: Z-L-ASPARTIC ACID DIBENZYL ESTER;Z-ASP(OBZL)-OBZL;CBZ-ASP(OBZL)-OBZL;CBZ-L-ASPARTIC ACID DIBENZYL ESTER;2-(benzyloxycarbonylamino)succinic acid bis(benzyl) ester;bis(phenylmethyl) 2-(phenylmethoxycarbonylamino)butanedioate;N-[(Phenylmethoxy)carbonyl]-L-aspartic acid 1,4-bis(phenylmethyl) ester;Z-L-Asp(OBzl)-OBzl
• CAS NO: 5241-60-1
• Molecular Formula: C₂₆H₂₅NO₆
• Molecular Weight: 447.48
• Mol File: 5241-60-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 611.7 °C at 760mmHg
• Flash Point: 323.7 °C
• Appearance: /
• Density: 1.234
• Vapor Pressure: 6.7E-15mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: CBZ-ASP(OBZL)-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: CBZ-ASP(OBZL)-OBZL(5241-60-1)
• EPA Substance Registry System: CBZ-ASP(OBZL)-OBZL(5241-60-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 5241-60-1(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C26H25NO6/c28-24(31-17-20-10-4-1-5-11-20)16-23(25(29)32-18-21-12-6-2-7-13-21)27-26(30)33-19-22-14-8-3-9-15-22/h1-15,23H,16-19H2,(H,27,30)

Upstream product

• 2886-33-1 dibenzyl L-aspartate toluene-4-sulphonate 
• 501-53-1 benzyl chloroformate 
• 56-84-8 L-Aspartic acid 
• 124-38-9 carbon dioxide 
• 100-44-7 benzyl chloride 
• 1152-61-0 N-Cbz-L-Asp 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 4515-21-3 N-benzyloxycarbonylaspartic acid 
• 620-05-3 iodomethylbenzene 

Downstream Products

• 39613-93-9 Z-Asp(OBzl)-D-AlaO(i-Pr) 
• 177288-62-9 (2S,3R)-2-Allyl-3-benzyloxycarbonylamino-succinic acid dibenzyl ester 
• 119278-21-6 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-leucine benzyl ester 
• 4526-73-2 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-aspartic acid dibenzyl ester 
• 104870-27-1 N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-glutamic acid dibenzyl ester 
• 5966-82-5 N²-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-N⁶-benzyloxycarbonyl-L-lysine benzyl ester 
• 5241-69-0 (N-Benzyloxycarbonyl-β-O-benzyl-Asp)-(β-phenyl-D-β-Ala)-amid 
• 5609-55-2 O-benzylaspartyl-phenylalanine amide 
• 5262-07-7 Z-Asp(OBzl)-Phe-OMe 
• 5241-68-9 Z-Asp(OBzl)-Phe-NH₂ 
• 5241-63-4 N-Benzyloxycarbonyl-L-asparaginsaeure-<α-(2,4,5-trichlor-phenyl)-β-benzyl-ester> 
• 4079-61-2 2-amino-succinic acid dibenzyl ester 
• 91647-54-0 N-Benzyloxycarbonyl-L-asparaginsaeure-dihydrazid 
• 29880-21-5 β-benzyl N-benzyloxycarbonyl-DL-aspartate 

Relevant articles and documents

First Practical Protection of α-Amino Acids as N, N-Benzyloxycarbamoyl Derivatives

The consecutive treatment of N-Cbz amino protected compounds with LiHMDS and CbzCl provides a practical method for the preparation of N,N-benzyloxycarbamoyl (N,N-di-Cbz) derivatives in good yield. When α-amino acids are used the protection occurs without racemization. The method is compatible with a wide range of other functional and protecting groups. The procedure is also valid for the synthesis of mixed N,N-carbamoyl derivatives.

Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl Chlorides

Several carbamate esters were synthesized from amines, carbon dioxide, and alkyl chlorides.The effect of added base on the yield and selectivity of carbamate ester formation was found to be highly important with the use of sterically hindered guanidine bases giving the best results.Relative rate studies were carried out giving the following order of reactivity between carbamate anions in acetonitrile with benzyl chloride giving carbamate esters: Et2NCO2(-) = Bu2NCO2(-) > t-BuNHCO2(-) = CyNHCO2(-) = s-BuNHCO2(-) > PhNHCO2(-) > CyCH2NHCO2(-) = n-octylNHCO2(-) = n-BuNHCO2(-).Rate studies were carried out with the diethyl, s-butyl, phenyl, and n-butyl carbamates and activation parameters were determined to be Et2NCO2(-), ΔH(excit.) = 11.8 kcal/mol, ΔS(excit.) = -33 eu; s-BuNHCO2(-), ΔH(excit.) = 12.8 kcal/mol, ΔS(excit.) = -33 eu; PhNHCO2(-), ΔH(excit.) = 14.3 kcal/mol, ΔS(excit.) = -28 eu; n-BuNHCO2(-), ΔH(excit.) = 23.4 kcal/mol, ΔS(excit.) = -3 eu.The unusual results obtained from the use of n-BuNHCO2(-) prompted further studies which showed that the rate of the reaction was inversely dependent on carbon dioxide pressure (20 psig CO2, k = 4.84E-4 M-1 s-1; 120 psig CO2, k = 1.83E-4 M-1 s-1).Nitrogen NMR spectroscopy indicated, via a labeling study with 15N amines and 13C enriched carbon dioxide, the formation of doubly inserted product from the addition of two carbon dioxides to ethylamine in acetonitrile.

Sequence peptide polymers. 3. Poly Asp(OH)-Ser(H)-Gly and other serine-containing polymers.

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