3886-08-6

Basic information

• Product Name: N-Cbz-L-Glutamic acid 5-tert-butyl ester
• Synonyms: 5-TERT-BUTYL N-CARBOBENZOXY-L-GLUTAMATE;5-TERT-BUTYL N-CBZ-L-GLUTAMATE;2-BENZYLOXYCARBONYLAMINO-4-TERT-BUTYLPENTANEDIOIC ACID;CBZ-GLU(OBUT)-OH;CBZ-GLU(OTBU)-OH;BENZYLOXYCARBONYL-L-GLUTAMIC ACID-T-BUTYL ESTER;BENZYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-ALPHA-CBZ-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER
• CAS NO: 3886-08-6
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.37
• EINECS: 223-421-3
• Product Categories: chiral;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Glutamic acid [Glu, E];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 3886-08-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 83-87 °C
• Boiling Point: 522.6 °C at 760 mmHg
• Flash Point: 269.9 °C
• Appearance: white to light yellow crystal powder
• Density: 1.197g/cm3
• Vapor Pressure: 9.49E-12mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: almost transparency in Methanol
• PKA: 3.80±0.10(Predicted)
• CAS DataBase Reference: N-Cbz-L-Glutamic acid 5-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-Glutamic acid 5-tert-butyl ester(3886-08-6)
• EPA Substance Registry System: N-Cbz-L-Glutamic acid 5-tert-butyl ester(3886-08-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 3886-08-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C17H23NO6/c1-17(2,3)24-14(19)10-9-13(15(20)21)18-16(22)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,20,21)/p-1/t13-/m0/s1

Upstream product

• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 23632-68-0 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester 
• 96762-62-8 γ-tert-Butyl-α-phthalimidomethyl-N-benzyloxycarbonyl-L-glutamat 
• 3967-18-8 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-benzyl ester 5-tert-butyl ester 
• 365217-97-6 5-tert-butyl 1-prop-2-en-1-yl 2-{[(benzyloxy)carbonyl]amino}-pentanedioate 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 

Downstream Products

• 3405-82-1 γ-tert.-Butyl-α-(2,4,5-trichlor-phenyl)-N-benzyloxycarbonyl-glutamat 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 162878-26-4 Z-Glu(O-t-Bu)-Thr(t-Bu)-Thr(t-Bu)-O-t-Bu 
• 4666-16-4 5-tert-butyl 1-(2,5-dioxopyrrolidin-1-yl) (S)-2-{[(phenylmethoxy)carbonyl]amino}glutarate 
• 287975-76-2 Z-Glu(OtBu)-Leu-Glu(OtBu)-NH₂ 
• 182237-06-5 C₅₁H₈₀N₆O₁₆ 
• 106930-52-3 S-4-benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 
• 130338-65-7 tert-butyl 4-<(benzyloxycarbonyl)amino>-5-(O-tosyl)pentanoate 
• 111491-74-8 C₅₀H₇₅N₉O₁₂S 

Relevant articles and documents

Enzymatic removal of carboxyl protecting groups. III. Fast removal of allyl and chloroethyl esters by Bacillus subtilis esterase (BS2)

(Chemical Equation Presented) An esterase from Bacillus subtilis (BS2) allows the fast and selective removal of allyl, 2-chloroethyl, and 2,2,2-chloroethyl esters under mild conditions in high yields. In addition, BS2 easily hydrolyzes phenacyl esters, while the hydrolysis of sterically hindered diphenylmethyl esters is slow, requiring longer reaction time and higher enzyme/substrate ratio.

Facile synthesis of tert-butyl ester of N-protected amino acids with tert-butyl bromide

A facile synthesis of a wide variety of N-benzyloxycarbonyl-amino acid-tert-butyl ester derivatives under mild conditions is described. N-protected amino acids were esterified with tert-butyl bromide in dimethylacetamide as solvent, in the presence of benzyltriethylammonium chloride (BTEAC)and a large excess of potassium carbonate. Many amino Z-acid-Tert-butyl esters that might be difficult to prepare by other methods have been synthesized in high yields by this procedure. The reaction is simple, unexpansive, easily scaled up, and proceeds without observable racemization.