7536-58-5

Usage

Uses

Used in Pharmaceutical Industry:
Boc-L-aspartic acid 4-benzyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason]. Its protected structure allows for the creation of complex molecules with specific functionalities, which can be crucial in the development of new drugs and therapies.
Used in Chemical Synthesis:
In the field of chemical synthesis, Boc-L-aspartic acid 4-benzyl ester is used as a building block for [application reason]. Its unique structure enables the formation of a wide range of chemical products, including specialty chemicals, agrochemicals, and advanced materials.
Used in Research and Development:
Boc-L-aspartic acid 4-benzyl ester is also employed as a research tool for [application reason]. Its availability and reactivity make it an ideal candidate for studying the properties and behavior of aspartic acid derivatives, which can lead to a better understanding of their biological and chemical roles.

InChI:InChI=1/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1

Upstream product

• 18595-34-1 tert-butyl fluoroformate 
• 2177-63-1 (S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 18942-25-1 t-butylpentachlorophenyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2886-33-1 dibenzyl L-aspartate toluene-4-sulphonate 
• 100-39-0 benzyl bromide 
• 30750-74-4 Boc-aspartic acid anhydride 
• 130052-01-6 α-2-cyanoethyl N(α)-tert-butoxycarbonyl-L-aspartate 
• 1361400-95-4 α-picolyl N-Boc-L-aspartate(OBn) 
• 13726-67-5 Boc-Asp-OH 
• 100-51-6 benzyl alcohol 
• 104-15-4 toluene-4-sulfonic acid 
• 149636-02-2 N-Boc-L-aspartic acid (β-benzyl) α-phenacyl ester 

Downstream Products

• 13726-67-5 Boc-Asp-OH 
• 68623-42-7 Boc-Glu(OBzl)-OH 
• 76144-15-5 1-benzyl 5-methyl (R)-3-tert-butoxycarbonylaminoglutarate 
• 80963-12-8 4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate 
• 80963-12-8 α-Methyl β-benzyl (2R)-N-(tert-butoxycarbonyl)aspartate diester 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 13798-75-9 N^α-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester 
• 26048-69-1 (S)-2-tert-Butoxycarbonylamino-succinic acid 4-benzyl ester 1-(4-nitro-phenyl) ester 
• 158010-97-0 Boc-Asp(β-OBzl)-Ser-OMe 
• 123836-67-9 N-(tert-butyloxycarbonyl)-L-aspartic acid β-benzyl-α-(trimethylsilyl)ethyl diester 
• 80963-08-2 N-tert-butoxycarbonyl-L-aspartic acid β-benzyl α-tert-butyl diester 
• 79722-12-6 N-Boc-β-Bzl-L-Asp-NHOBzl 
• 68763-45-1 N-(tert-Butoxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine 
• 155279-46-2 Boc-L-Asp(OBzl)-NH-p-tolyl 

Relevant academic research and scientific papers

Supramolecular nanocarrier of siRNA from PEG-based block catiomer carrying diamine side chain with distinctive pKa directed to enhance intracellular gene silencing

An siRNA nanocarrier formed through self-assembly of PEG-based block catiomer possessing two distinct amino groups with different pKa values in a side chain was developed. This design provided the carrier with a sufficient siRNA complexation and an assumed buffering capacity in the endosomes, allowing it to exhibit remarkable gene knockdown abilities as well as sufficient serum tolerability. Copyright

DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS

The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexatnethylenediaanine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 -9 to 10 -5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.

Cathepsin K inhibitors and use thereof

The invention relates to compounds and pharmaceutical compositions thereof for treatment or prevention of cathepsin dependent diseases; the compounds and the compositions comprising the compounds can be used as bone absorption inhibitors for treatment of related diseases, wherein the cathepsin includes, but is not limited to, cathepsin K.

Controlled ring-opening polymerization of α-amino acid N-carboxy-anhydride by frustrated amine/borane Lewis pairs

In this communication, we presented a novel strategy to control the ROP of α-amino acid N-carboxy-anhydrides using the concept of frustrated Lewis pairs (FLPs). An FLP intermediate containing an interaction between the bulky borane Lewis acid and the amine groups of the propagation chain end is essential to accomplish the polypeptide synthesis with well-defined structures under mild conditions.

N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis

A series of N-pyrrolidine-based α,β-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2]octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that played a determinant role. Among the peptides tested, the heterochiral tripeptide H-Pro-(R)-ABOC-Asp-OCH3 13, that adopts a turn conformation in the solid state, proved to be the most efficient catalyst affording β-hydroxy ketones in high yields and good enantioselectivities (up to 87%).

Heating reactions of N-t-Butyloxycarbonyl-Asparagine and related compounds

N-t-Butyloxycarbonyl-amino acids (Boc-) are labile on heating to afford free amino acids, but Boc-aspartic acid gives a kind of polypeptide. This chemical feature of Boc-aspartic acid may be caused by dehydration between two carboxyl groups as well as the formation of a free amino group. Boc-Asparagine may have a similar reactivity to Boc-aspartic acid. This research describes polypeptide formation by heating Boc-asparagine and its isomer Boc-aspartic acid amide.

A mild method for the cleavage of the 4-picolyloxy group with magnesium under neutral conditions

A mild and efficient method for the selective hydrolysis of 4-picolyl esters with magnesium in methanol or water in the presence of other esters and sensitive protecting groups is described. 4-Picolyl aryl ethers and thioethers are also smoothly deprotected to give the corresponding phenols and thiophenols. Georg Thieme Verlag Stuttgart. New York.

Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 μM) and in vivo antithrombotic efficacy.

Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors

A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (β5) activity (IC50 = 0.28 and 0.51 μM, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 μM concentrations of compound.

Asymmetric dieckmann condensation via memory of chirality: synthesis of the key intermediate for as-3201, an aldose reductase inhibitor

Asymmetric Dieckmann condensation via memory of chirality has been developed. A key intermediate for the synthesis of AS-3201, an aldose reductase inhibitor, has been prepared in 94% ee by asymmetric Dieckmann condensation of 8 derived from L-aspartic acid.