71989-18-9

Basic information

• Product Name: Fmoc-L-glutamic acid 5-tert-butyl ester
• Synonyms: N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMIC-ACID-GAMMA-T-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-GAMMA-T-BUTYL-L-GLUTAMIC ACID;N-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-FMOC-O-T-BUTYL-L-GLU
• CAS NO: 71989-18-9
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.47
• EINECS: 276-253-8
• Product Categories: Amino Acid Derivatives;Amino Acids;Glutamic acid [Glu, E];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series;Pyridines
• Mol File: 71989-18-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 83-90 °C
• Boiling Point: 638.1 °C at 760 mmHg
• Flash Point: 339.7 °C
• Appearance: White powder
• Density: 1.232 g/cm³
• Vapor Pressure: 3.72E-17mmHg at 25°C
• Refractive Index: -4 ° (C=1, 80% AcOH)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 3.70±0.10(Predicted)
• BRN: 3636375
• CAS DataBase Reference: Fmoc-L-glutamic acid 5-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-glutamic acid 5-tert-butyl ester(71989-18-9)
• EPA Substance Registry System: Fmoc-L-glutamic acid 5-tert-butyl ester(71989-18-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 71989-18-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Fmoc-Glu(OtBu)-OH (Fmoc-L-glutamic acid 5-tert-butyl ester) can be employed as a: Ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst.Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives.It can be also used as a building block in the preparation of stapled α-helical peptides , and peptide C-terminal thioesters .

General Description

The product number for this product was previously 04-12-1020.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

InChI:InChI=1/C24H27NO6/c1-24(2,3)31-22(28)20(12-13-21(26)27)25-23(29)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t20-/m0/s1

Upstream product

• 2419-56-9 L-glutamic acid 5-tert-butyl ester 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 56-86-0 L-glutamic acid 
• 115-11-7 isobutene 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 851713-96-7 Fmoc-Glu(t-Bu)-1,1-dimethylallyl ester 

Downstream Products

• 86061-04-3 N^α-Fmoc-Glu-(O-tBu)-OPfp 
• 114119-86-7 Fmoc-Glu(OtBu)-OObt 
• 154672-63-6 Benzyl ester of α-N-(9-fluorenylmethoxycarbonyl)-γ-tert-butyl ester of L-glutamic acid 
• 920289-92-5 Fmoc-L-Glu(OtBu)-OH 
• 319494-39-8 Ac-VEID-CHO 

Relevant articles and documents

High-efficiency industrial production method of Fmoc-Glu (Otbu)-OH

The invention relates to the field of organic synthesis, and especially relates to the technical field of a high-efficiency industrial production method of Fmoc-Glu (Otbu)-OH. The method comprises thefollowing steps: synthesizing an intermediate [Glu(OtBu)]2Cu, and then synthesizing the target product Fmoc-Glu (Otbu)-OH. The method has the advantages of great reduction of reaction steps, and goodcontrol of the reaction process. The industrial production method of the Fmoc-Glu (Otbu)-OH can efficiently and stably produce the high-quality Fmoc-Glu (Otbu)-OH, so the purity is greater than 99.5%, and the content of a single impurity is less than 0.1%.

Synthesis of l -octaarginine through microencapsulated palladium-catalyzed allyl ester deprotection

Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.

Efficient procedure for the preparation of oligomer-free N-fmoc amino acids

A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.