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

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 
• 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 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 23632-67-9 (S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid 
• 23632-68-0 4(S)-(2-tert-butoxycarbonylethyl)-5-oxo-oxazolidine 3-carboxylic acid benzyl ester 

Downstream Products

• 7670-08-8 (benzyloxycarbonyl)-γ-tert-butyl-L-glutamic acid p-nitrophenyl ester 
• 101698-49-1 Z-Glu-Thr-OMe 
• 17337-66-5 N-Benzyloxycarbonyl-γ-O-tert.-butyl-Glu-Phe-amid 
• 31025-16-8 Z-Phe-Glu(OCMe₃)-OCH₃ 
• 24181-32-6 N-benzyloxycarbonyl-γ-tert-butyl-L-glutamyl-L-leucine methyl ester 
• 2419-56-9 L-glutamic acid 5-tert-butyl ester 
• 17191-52-5 tert-butyl (4S)-5-amino-4-(benzyloxycarbonylamino)-5-oxo-pentanoate 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 157886-25-4 Z-Glu(Ot-Bu)-Asp(Ot-Bu)-OMe 
• 51537-19-0 Z-L-Glu(OtBu)-L-Ser(tBu)-OtBu 
• 120092-03-7 methyl benzyloxycarbonyl (γ-t-butyloxy)glutamyl-γ-aminobutyrate 
• 3967-22-4 N^α-benzyloxycarbonyl(γ-tert-butyl)glutamylhistidine methyl ester 
• 153037-21-9 4(S)-benzyloxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester 
• 128633-24-9 Z-Glu(OBu^t)-D-Phe-Lys(Boc)-D-Trp-OMe 

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.

Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties

Enzymes are versatile reagents for the efficient removal of methyl and benzyl protecting groups. An esterase from Bacillus subtilis (BS2) and a lipase from Candida antarctica (CAL-A) allow a mild and selective removal of these moieties in high yields without affecting other functional groups.

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.

TERT-BUTYL ESTERS OF N-PROTECTED AMINO ACIDS WITH TERT-BUTYL FLUOROCARBONATE (Boc-F)

Tert-butyl fluorocarbonate (Boc-F) is efficiently used for the synthesis of tert-butyl esters of N-protected amino acids.The reaction proceeds at room temperature and under mild conditions in the presence of triethylamine and 4-dimethylamino-pyridine.