127357-38-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its role is pivotal in the development of new drugs for the treatment of a wide array of diseases, providing a structural foundation that can be modified to target specific biological pathways.
Used in Organic Synthesis as a Reagent:
In the realm of organic synthesis, methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate functions as a reagent, especially in the preparation of peptides and other organic compounds. Its ability to form stable intermediates and participate in various chemical reactions makes it a valuable tool for creating complex organic molecules.
Used in the Development of Peptide-based Therapies:
Given its structural similarity to glycine, a common amino acid in peptides, methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate is used in the development of peptide-based therapies. Its unique properties allow for the creation of modified peptides with enhanced stability and bioactivity, which can be crucial for therapeutic applications.
Used in Chemical Research:
Methyl 2-(benzyloxycarbonylamino)-2-hydroxyacetate is also employed in chemical research to explore new reaction pathways and mechanisms. Its reactivity and the ease with which it can be modified make it an ideal candidate for studying the fundamental aspects of organic chemistry and the development of novel synthetic methods.

Upstream product

• 67-56-1 methanol 
• 621-84-1 O-benzyl carbamate 
• 563-96-2 2,2-dihydroxyacetic acid 
• 186581-53-3 diazomethane 
• 79002-45-2 N-benzyloxycarbonyl-glycine 
• 5162-44-7 1-bromo-4-butene 
• 64356-76-9 N-benzyloxycarbonyl α-chloro glycine methyl ester 
• 74-96-4 ethyl bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 593-60-2 Vinyl bromide 
• 2003-82-9 3-bromo-2-propyne 
• 557-93-7 2-bromoprop-1-ene 
• 13294-71-8 2-bromo-but-2-ene 
• 598-73-2 1-bromo-1,2,2-trifluoroethene 

Downstream Products

• 64356-76-9 N-benzyloxycarbonyl α-chloro glycine methyl ester 
• 127382-97-2 methyl N-(benzyloxycarbonyl)-α-bromoglycinate 
• 160380-85-8 α-azido-N-(benzyloxycarbonyl)glycine methyl ester 
• 42726-78-3 methyl N-benzyloxycarbonyl-α-benzylthioglycinate 
• 88259-97-6 2-carbobenzyloxy-3-carbomethoxy-2-azabicyclo<2.2.1>heptane 
• 99940-87-1 2-carbobenzyloxy-3-carbomethoxy-2-azabicyclo<2.2.1>hept-5-ene 
• 127357-69-1 methyl 2-amino-N-(benzyloxycarbonyl)-3-butynoate 
• 119839-50-8 methyl 2-amino-N-(benzyloxycarbonyl)-3-pentynoate 
• 119839-48-4 methyl 2-amino-N-(benzyloxycarbonyl)-3-heptynoate 
• 127357-39-5 methyl 2-amino-N-(benzyloxycarbonyl)-4-(trimethylsilyl)-3-butynoate 
• 127357-42-0 methyl 2-amino-N-(benzyloxycarbonyl)-3-octynoate 
• 119839-51-9 methyl 2-amino-N-(benzyloxycarbonyl)-4-phenyl-3-butynoate 
• 127357-43-1 methyl 2-amino-N-(benzyloxycarbonyl)-3-decynoate 
• 127357-45-3 methyl 2-amino-N-(benzyloxycarbonyl)-6-<(tert-butyldimethylsilyl)oxy>-3-hexynoate 

Relevant academic research and scientific papers

NOVEL PEPTIDE DERIVATIVES AND USES THEREOF

The invention provides for novel peptide derivatives and compositions comprising the same. The invention further provides methods of treatment comprising administering novel peptide derivatives and/or compositions comprising the same.

Lanthanide (III) complexes that contain a self-immolative arm: Potential enzyme responsive contrast agents for magnetic resonance imaging

Enzyme-responsive MRIcontrast agents containing a "self- immolative" benzylcarbamate moiety that links the MRI-reporter lanthanide complex to a specific enzyme substrate have been developed. The enzymatic cleavage initiates an electronic cascade reaction that leads to a structural change in the LnIII complex, with a concomitant response in its MRI-contrast- enhancing properties. We synthesized and investigated a series of Gd3+ and Yb3+ complexes, including those bearing a self-immolative arm and a sugar unit as selective substrates for bgalactosidase; we synthesized complex LnL1, its NH2 amine derivatives formed after enzymatic cleavage, LnL2, and two model compounds, LnL3 and LnL4. All of the Gd3+ complexes synthesized have a single inner-sphere water molecule. The relaxivity change upon enzymatic cleavage is limited (3.68 vs. 3.15 mm-1 s-1 for complexes GdL1 and GdL2, respectively; 37 °C, 60 MHz), which prevents application of this system as an enzyme-responsive T1 relaxation agent. Variable-temperature 17O NMR spectroscopy and 1H NMRD (nuclear magnetic relaxation dispersion) analysis were used to assess the parameters that determine proton relaxivity for the Gd 3+ complexes, including the water-exchange rate (kex 298, varies in the range 1.5-3.9×106 s -1). Following the enzymatic reaction, the chelates contain an exocyclic amine that is not protonated at physiological pH, as deduced from pH-potentiometric measurements (log KH=5.12(±0.01) and 5.99(±0.01) for GdL2 and GdL3, respectively). The Yb3+ analogues show a PARACEST effect after enzymatic cleavage that can be exploited for the specific detection of enzymatic activity. The proton-exchange rates were determined at various pH values for the amine derivatives by using the dependency of the CEST effect on concentration, saturation time, and saturation power. A concentration-independent analysis of the saturation-power-dependency data was also applied. All these different methods showed that the exchange rate of the amine protons of the Yb III complexes decreases with increasing pH value (for YbL 3, kex= 1300 s-1 at pH 8.4 vs. 6000 s -1 at pH 6.4), thereby resulting in a diminution of the observed CEST effect.

Synthesis of differently protected α-aminoglycines and their peptide derivatives

Compatibly protected α-aminoglycine and di- and tripeptides containing it are prepared from the corresponding α-hydroxyglycines.

General Synthesis of β,γ-Alkynylglycine Derivatives

The coupling of α-haloglycinates 8 with alkynyltin reagents produces the fully protected β,γ-alkynylglycines 9.Subsequent deprotection of the amino or carboxyl groups generates differentially protected β,γ-alkynylglycine derivatives 10-14.The free amino a

SYNTHESIS OF α-AMINO ACIDS WITH β,γ-UNSATURATED SIDE CHAINS

α-Amino acids with allenyl, vinyl and acetylenic side chains can be synthesized using non-enolate based strategies.The ester enolate-Claisen rearrangement applied to propargylic esters of N-protected α-amino acids is of limited utility since only poor yields of allenic product are obtained with the N-Boc glycine esters, the system which give the most reproducible results.However, α-allenyl-α-amino acids that are fully functionalized on the α-carbon are available through the agency of 4-allenyl-2-phenyloxazolones 4 ( obtained from propargyl esters of N-benzoyl protected amino acids via cyclization and Claisen rearrangement ) provided that Meerwein's reagent is used to facilitate hydrolysis of the benzamide function in 5.A variety of α-substituted glycinates, including those with α-vinyl and α-acetylenic functions, can be prepared using a two step sequence involving condensation of the cationic glycine synthon 22 with various organomagnesium reagents, followed by hydrolysis.

2-Azabicycloheptane-3-carboxylic Acid - A Bicyclic Proline

Diels-Alder reaction of cyclopentadiene and methyl N-carbobenzyloxy-2-iminoacetate generated in situ from methyl 2-chloro-N-carbobenzyloxyglycinate by triethylamine gave the N-carbobenzyloxy unsaturated bicyclic proline ester.This was converted in two ste