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59279-60-6

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59279-60-6 Usage

Description

(R)-N-Boc-glutamic acid-1,5-dimethyl ester is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals and chemicals. It is characterized by its unique molecular structure, which includes a Boc-protected glutamic acid backbone with two methyl ester groups at the 1 and 5 positions. (R)-N-Boc-glutamic acid-1,5-dimethyl ester is known for its stability and reactivity, making it a valuable building block in the development of new drugs and chemical products.

Uses

Used in Pharmaceutical Industry:
(R)-N-Boc-glutamic acid-1,5-dimethyl ester is used as a pharmaceutical intermediate for the development of new drugs. Its unique structure allows for the creation of novel compounds with potential therapeutic applications, contributing to the advancement of medical treatments.
Used in Chemical Production Processes:
(R)-N-Boc-glutamic acid-1,5-dimethyl ester is also utilized as an organic synthesis intermediate in the chemical industry. Its versatility in chemical reactions enables the production of a wide range of chemical products, from specialty chemicals to advanced materials.
Used in Laboratory Research and Development:
In addition to its industrial applications, (R)-N-Boc-glutamic acid-1,5-dimethyl ester is a valuable compound for laboratory research and development. Its unique properties make it an ideal candidate for studying various chemical reactions and exploring new synthetic pathways, further expanding the knowledge and capabilities within the scientific community.

Synthesis

L-glutamic acid (10.0 g, 67.97 mmol) was dissolved in 200 mL of methanol, and SOCl2(10.85 mL, 149.53 mmol)was slowly added dropwise under an ice bath. After the addition, reflux was performed at 65 ° C. After 2 hours, the reaction system was cooled to room temperature, and methanol was evaporated to dryness under reduced pressure to obtain a colorless viscous substance.This colorless viscous substance was dissolved in 200 mL of THF, (Boc)2O (22.25 g, 101.95 mmol) was addedunder an ice bath, and triethylamine (14.13 mL, 101.95 mmol) was slowly added dropwise.After the addition was complete, the reaction was allowed to proceed at room temperature overnight.After completion of the reaction, the solvent was distilled off under reduced pressure.The residue was dissolved in 200 mL of dichloromethane.The organic phase was washed with water (200 mL * 2), saturated citric acid solution (200 mL * 2), saturated sodium bicarbonate solution (200 mL * 2), and saturated brine (200 mL * 2) in that order.The organic phase was dried over anhydrous Na2SO4. Thefiltrate was collected by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 4: 1 v / v) to give a colorless oily product 2 (18.34 g, yield 98%)

Check Digit Verification of cas no

The CAS Registry Mumber 59279-60-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,2,7 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 59279-60:
(7*5)+(6*9)+(5*2)+(4*7)+(3*9)+(2*6)+(1*0)=166
166 % 10 = 6
So 59279-60-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H21NO6/c1-12(2,3)19-11(16)13-8(10(15)18-5)6-7-9(14)17-4/h8H,6-7H2,1-5H3,(H,13,16)/t8-/m0/s1

59279-60-6 Well-known Company Product Price

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  • TCI America

  • (D4536)  Dimethyl N-(tert-Butoxycarbonyl)-L-glutamate  >98.0%(HPLC)(N)

  • 59279-60-6

  • 1g

  • 280.00CNY

  • Detail
  • TCI America

  • (D4536)  Dimethyl N-(tert-Butoxycarbonyl)-L-glutamate  >98.0%(HPLC)(N)

  • 59279-60-6

  • 5g

  • 980.00CNY

  • Detail
  • Alfa Aesar

  • (H62056)  N-Boc-L-glutamic acid 1,5-dimethyl ester, 97%   

  • 59279-60-6

  • 5g

  • 470.0CNY

  • Detail
  • Alfa Aesar

  • (H62056)  N-Boc-L-glutamic acid 1,5-dimethyl ester, 97%   

  • 59279-60-6

  • 25g

  • 1882.0CNY

  • Detail

59279-60-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name dimethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate

1.2 Other means of identification

Product number -
Other names tert-butoxycarbonyl L-glutamic acidd imethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59279-60-6 SDS

59279-60-6Relevant articles and documents

Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine

supporting information, p. 2260 - 2268 (2021/03/04)

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

Selenolysine: A New Tool for Traceless Isopeptide Bond Formation

Dardashti, Rebecca Notis,Kumar, Shailesh,Sternisha, Shawn M.,Reddy, Post Sai,Miller, Brian G.,Metanis, Norman

supporting information, p. 4952 - 4957 (2020/04/07)

Despite their biological importance, post-translationally modified proteins are notoriously difficult to produce in a homogeneous fashion by using conventional expression systems. Chemical protein synthesis or semisynthesis offers a solution to this problem; however, traditional strategies often rely on sulfur-based chemistry that is incompatible with the presence of any cysteine residues in the target protein. To overcome these limitations, we present the design and synthesis of γ-selenolysine, a selenol-containing form of the commonly modified proteinogenic amino acid, lysine. The utility of γ-selenolysine is demonstrated with the traceless ligation of the small ubiquitin-like modifier protein, SUMO-1, to a peptide segment of human glucokinase. The resulting polypeptide is poised for native chemical ligation and chemoselective deselenization in the presence of unprotected cysteine residues. Selenolysine's straightforward synthesis and incorporation into synthetic peptides marks it as a universal handle for conjugating any ubiquitin-like modifying protein to its target.

Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers

Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine

supporting information, (2020/09/01)

Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).

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