16874-06-9

Basic information

• Product Name: L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT
• Synonyms: bis(tert-butyl) L-glutamate;Glutamicaciddi-tert-butylesterdibenzenesulfimidesalt;di-tert-butyl glutamate;L-glutamic acid di-tert-butyl ester dibenzenesulfimide;L-Glutamic acid di-tert-butyl ester dibenzenesulfonimide salt;L-Glutamic acid bis(1,1-dimethylethyl) ester;Einecs 240-900-2;L-GlutaMic acid di-tert-butyl ester
• CAS NO: 16874-06-9
• Molecular Formula: C₁₃H₂₅NO₄
• Molecular Weight: 259.3419
• EINECS: 240-900-2
• Product Categories: Amino Acid Derivatives;Glutamic Acid;Peptide Synthesis
• Mol File: 16874-06-9.mol

Chemical Properties

• Melting Point: 139-141 °C (dec.)
• Boiling Point: 311.1°Cat760mmHg
• Flash Point: 78.1°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 0.000574mmHg at 25°C
• Refractive Index: 1.457
• PKA: 6.85±0.35(Predicted)
• CAS DataBase Reference: L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT(CAS DataBase Reference)
• NIST Chemistry Reference: L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT(16874-06-9)
• EPA Substance Registry System: L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT(16874-06-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 16874-06-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT is used as a chemical intermediate for its ability to participate in various chemical reactions, facilitating the synthesis of a range of organic compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT is used as a building block in the synthesis of peptides and other biologically active compounds, contributing to the development of new pharmaceutical agents.
Used in Pharmaceutical Industry:
L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT is utilized in the pharmaceutical industry as a component in drug development, where its unique properties are leveraged to create novel therapeutics with potential applications in treating various medical conditions.

InChI:InChI=1/C13H25NO4/c1-12(2,3)17-10(15)8-7-9(14)11(16)18-13(4,5)6/h9H,7-8,14H2,1-6H3/t9-/m0/s1

Upstream product

• 16881-41-7 di-tert-butyl N-Cbz-L-glutamate 
• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 540-88-5 acetic acid tert-butyl ester 
• 56-86-0 L-glutamic acid 
• 86491-34-1 Di-tert-butyl α-ketoglutarate 
• 1197815-07-8 C₃₉H₅₅N₃O₁₁Se 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 115-11-7 isobutene 

Downstream Products

• 32719-56-5 tri-tert-butyl N--L-glutamate 
• 124688-46-6 N-<4-(N-Cbz-D,L-erythro,threo-5-oxo-4-oxazolidinyl)-2-fluoropropionyl>-L-glutamic acid di-tert-butyl ester 
• 87597-84-0 di-tert-butyl N-(4-formylbenzoyl)-L-glutamate 
• 113035-38-4 Boc-L-Phe-L-Glu(OtBu)-OtBu 
• 120296-66-4 di-tert-butyl-5-chloro-N¹⁰-(trifluoroacetyl)-5,8-dideazafolate 
• 247167-08-4 N-(2-nitrobenzenesulfonyl)-L-glutamic acid di-t-butyl ester 
• 108947-92-8 (S)-2-{4-[(2-Amino-5-chloro-4-hydroxy-quinazolin-6-ylamino)-methyl]-benzoylamino}-pentanedioic acid; compound with trifluoro-acetic acid 
• 108947-93-9 (S)-2-{4-[(2,4-Diamino-5-chloro-quinazolin-6-ylamino)-methyl]-benzoylamino}-pentanedioic acid; compound with trifluoro-acetic acid 
• 1140408-20-3 di-tert-butyl 2-(2-(5-benzyl-6-oxo-3-phenylpyridazin-1(6H)-yl)acetamido)pentanedioate 
• 1197815-08-9 C₂₉H₃₈N₂O₈Se 
• 1197815-06-7 C₂₅H₃₈N₂O₈Se 
• 1270004-63-1 4'-O-CO-Ala-[Glu(OtBu)-OtBu]-tricin 
• 1270004-53-9 4'-O-CO-[Glu(OtBu)-OtBu]-tricin 
• 1270004-61-9 4'-O-CO-Glu-tricin 

Relevant articles and documents

Radiosynthesis of novel N-18F-labeled 18F-FHex-α-l-Glu and 18F-FHex-β-Glu

N-18F-labeled amino acids are important substitutes for new positron emission tomography (PET) imaging tracers complementing the deficiency of 18F-fluorodeoxyglucose (18F-FDG). In this work, two novel N-6-18F-alkyl amino acid imaging agents, 18F-FHex-α-l-Glu and 18F-FHex-β-Glu, were designed and synthesized as potential probes for PET imaging of tumors. 18F-FHex-α-l-Glu was synthesized using the precursor 6 from 18F-F? with the yield of 16 ± 4% (n = 5, uncorrected) within about 50 minutes. The specific activity was 14.5 GBq/μmol, and the radiochemical purity was more than 95%. 18F-FHex-β-Glu was synthesized using the precursor 12 based on 18F-F? with the yield of 11 ± 3% (n = 3, uncorrected) in about 60 minutes. The specific activity was 9.1 GBq/μmol, and the radiochemical purity was more than 95%.

Efficient Synthesis of a Family of Bifunctional Chelators Based on the PCTA[12] Macrocycle Suitable for Bioconjugation

PCTA[12] is a 12-membered tetraaza-macrocyclic ligand that incorporates a pyridine unit within the macrocyclic ring and three acetate pendant arms. Unlike DOTA and NOTA chelators, PCTA is a recent entry to the field of macrocyclic polyaminocarboxylate ligands available to complex a variety of M2+/M3+ ions for biomedical applications such as diagnostic and radiotherapeutic. Despite the promising properties of its chelates, only a few of bifunctional chelating agents (BFCAs) derived from PCTA have been described so far. Based on our very recent methodology for the preparation of PCTA[12] itself, we report here the efficient synthesis of several BFCAs derived from PCTA bearing a free reactive function group, mainly devoted to conjugation purposes: ester, carboxylic acid, alcohol, aliphatic amine, aromatic amine, maleimide, bromo or azide functions. These functions were introduced either on the 4-position of the pyridine ring or on the methylene carbon atom of the central acetate chelating arm, while keeping the three carboxylate groups available for metal chelation. Moreover, two of these BFCAs-PCTA were used for conjugation with a tetrapeptide (cholecystokinin analogue), a bioactive molecule (biotin), or a solid support (silica gel).

Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination

A biomimetic enantioselective transamination of α-keto ester derivatives can be realized under mild conditions by using chiral quaternary ammonium arenecarboxylates in the absence of base additives. The corresponding α-amino acids can be used as versatile intermediates for further synthetic transformations that furnish chiral pyrrolidine and octahydroindolizine derivatives.

PRODRUGS ACTIVATED BY REACTIVE OXYGEN SPECIES FOR USE IN THE TREATMENT OF INFLAMMATORY DISEASES AND CANCER

Prodrugs activated predominantly or exclusively in inflammatory tissue, more particularly prodrugs of methotrexate and derivatives thereof, which are selectively activated by Reactive Oxygen Species (ROS) in inflammatory tissues associated with cancer and inflammatory diseases, as well as method for preparing said prodrugs.

A selenide-based approach to photochemical cleavage of peptide and protein backbones at engineered backbone esters

(Chemical Equation Presented) A strategy for photochemical cleavage of peptide and protein backbones is described, which is based on a selenide-mediated cleavage of a backbone ester moiety. Studies in model systems establish the viability of the chemistry

A higher yielding synthesis of the clinical prodrug ZD2767P using di-protected 4-[N,N-bis(2-hydroxyethyl)amino]phenyl chloroformate

A novel synthesis is described of the prodrug ZD2767P (in Phase I/II clinical trials) that improves the overall yield from 13% to 45%. The method involves the synthesis of 4-[N,N-bis(2-hydroxyethyl)amino]phenyl chloroformate protected as the bis-silyl ether, coupled with di-tert-butyl glutamate. There are clear advantages of this method compared to the literature procedure.

INHIBITORS OF GLYCINAMIDE RIBONUCLEOTIDE TRANSFORMYLASE

Potent human inhibitors of human glycinamide ribonucleotide transformylase and of aminoimidazole carboxamide ribonucleotide transformylase are designed, synthesized, and characterized.