59768-74-0

Basic information

• Product Name: Boc-L-aspartic acid 4-methyl ester
• Synonyms: Boc-L-aspartic acid beta-Methyl ester;Boc-L-aspartic acid beta-Methyl ester dicyclohexylaMMoniuM salt;N-Boc-L-aspartic acid 4-Methyl ester dicyclohexylaMMoniuM salt, 95%;Boc-Asp(OMe)-OH >=98.0% (TLC);Boc-L-Asp(OMe)-OH;Boc-L-Asp(OMe)-OH·DCHA;Boc-L-aspartic acid b-methyl ester dicyclohexylammonium salt≥ 98% (HPLC);Boc-L-aspartic acid β-methyl ester≥ 99% (HPLC)
• CAS NO: 59768-74-0
• Molecular Formula: C₁₀H₁₇NO₆
• Molecular Weight: 247.25
• Product Categories: Boc-Amino Acids;Amino Acid Derivatives;Aspartic acid [Asp, D];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 59768-74-0.mol

Chemical Properties

• Boiling Point: 411.523 °C at 760 mmHg
• Flash Point: 202.682 °C
• Appearance: Clear colorless to yellow/Solution
• Density: 1.209 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.47
• Storage Temp.: −20°C
• BRN: 4810472
• CAS DataBase Reference: Boc-L-aspartic acid 4-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-aspartic acid 4-methyl ester(59768-74-0)
• EPA Substance Registry System: Boc-L-aspartic acid 4-methyl ester(59768-74-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59768-74-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-L-aspartic acid 4-methyl ester is used as a key intermediate in the synthesis of isoxazoline glycoprotein IIb/IIIa antagonists. These antagonists play a crucial role in inhibiting platelet aggregation, which is essential for the prevention and treatment of thrombotic disorders.
Additionally, Boc-L-aspartic acid 4-methyl ester is utilized as a building block for the synthesis of glutamic acid analogs. These analogs have been identified as potent inhibitors of leukotriene A4 hydrolase, an enzyme involved in the production of inflammatory mediators. Inhibiting this enzyme can help in the development of anti-inflammatory drugs for the treatment of various conditions, such as asthma and other inflammatory diseases.

InChI:InChI=1/C10H17NO6/c1-10(2,3)17-9(15)11-6(8(13)14)5-7(12)16-4/h6H,5H2,1-4H3,(H,11,15)(H,13,14)/t6-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 16856-13-6 (+)-β-methyl-L-aspartate hydrochloride 
• 30925-18-9 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 
• 784191-90-8 methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate 
• 1054666-03-3 (3S,4S)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-pentanoic acid methyl ester 
• 2177-62-0 β-methyl L-aspartate 
• 158201-15-1 α-benzyl β-methyl N^α-tert-butoxycarbonyl-(S)-aspartate 
• 67-56-1 methanol 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 

Downstream Products

• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 
• 848555-72-6 C₂₀H₂₈N₂O₇ 
• 158201-15-1 α-benzyl β-methyl N^α-tert-butoxycarbonyl-(S)-aspartate 
• 881995-73-9 3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester 

Relevant articles and documents

Stereoselective Synthesis of Protected l - Allo -Enduracididine and l -Enduracididine via Asymmetric Nitroaldol Reaction

The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l - allo -enduracididine and l -enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l -aspartic acid. The cyclic guanidine of di-Cbz-protected l - allo -enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.

Process for preparing deuterated desmosine and derivatives thereof

There is provided a process for preparing a compound represented by the following general formula (1) or a salt thereof, which comprises exchanging one or more of an amino proton in a compound represented by the following general formula (2) or a salt thereof to deuterium, and after the exchanging, converting a deuterium-exchanged compound of the compound represented by the general formula (2) or a salt thereof into the compound represented by the general formula (1) or a salt thereof: wherein, in the general formula (1), one, or two or more of hydrogen atom may be substituted with their isotope; and in the general formula (2), each of R1 is independently hydrogen atom, tert-butyloxycarbonyl group or benzyloxycarbonyl group, and R2 is independently tert-butyl group, benzyl group, methyl group or ethyl group.

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

Synthesis of desmosine-d4: Improvement of isotopic purity by D-H exchange of amino groups

Desmosine is a crosslinking pyridinium amino acid of elastin, which is a useful biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD) by LC–MS/MS analysis. We previously reported a synthesis of desmosine-d4, which is useful as an internal standard for quantitative LC–MS/MS analysis of desmosines, by deuterogenation of an alkyne group; however, the isotopic purity of the desmosine-d4was only ca. 50%. The present report describes a new synthesis of desmosine-d4that improves the isotopic purity to ca. 90% by exchanging the protons of the amino groups to deuterium using deuterogenation.

A 10th factor inhibitor and its preparation method and application (by machine translation)

The invention relates to a 10th factor inhibitor and its preparation and application, the 10th factor inhibitor has the structure of formula I, the invention inhibitors to alpha-amino acid as a template, respectively through the amide, carbamate, or urea to the branched chain is formed by a series of novel structure of the compound, this kind of compound can be effectively with the 10th factor binding, prevent the formation of thrombus. (by machine translation)

Facile synthesis of urea-and thiocarbamate-tethered glycosyl beta-amino acids

We describe here an efficient way to synthesize series of new urea- and thiocarbamate-tethered glycosyl β-amino acids under mild conditions. These glycosyl β-amino acids are elaborately designed on the basis of natural N-linked glycosides. They have the same side chain length as natural N-glycosyl amino acid while the main chain is replaced with β-amino acid chain. The linkage is an isostere of natural N-linked bond but exhibits competitive stability to chemical and enzymatic hydrolysis. This facile route is benefit from the choice of the commercially available l-aspartic acid as starting material, which not only provides a β-amino acid moiety, but also the α-carboxy group could be transformed to active isocyanate conveniently and economically. The prospective glycosyl β-amino acids are obtained readily by the reaction of isocyanate with appropriately protected glycosylamines and glycosylthiols.

VERSATILE AND STEREOSPECIFIC SYNTHESIS OF GAMMA,DELTA -UNSATURATED AMINO ACIDS BY WITTIG REACTION

The present invention relates to γ,δ-unsaturated a-amino acids of general formula (I). The present invention also provides a versatile process for the stereospecific synthesis of said compounds of formula (I), involving a Wittig reaction. The present invention also relates to intermediate products of general formulae (II) and (III), as shown below, which are involved in the synthesis of compounds (I).

Stereoselective synthesis of unsaturated and functionalized L-NHBoc amino acids, using wittig reaction under mild phase-transfer conditions

The stereoselective synthesis of a new amino acid phosphonium salt was described by quaternization of melting triphenylphosphine with the β-iodo NHBoc-amino ester, derived from l-aspartic acid. The deprotection of the carboxylic acid function to afford the phosphonium salt with a free carboxylic acid group was achieved by a palladium-catalyzed desallylation reaction. This phosphonium salt was used in the Wittig reaction with aromatic or aliphatic aldehydes and trifluoroacetophenone, under solid-liquid phase-transfer conditions in chlorobenzene and in the presence of K3PO4 as weak base, to afford the corresponding unsaturated amino acids without racemization. Thus, the reaction with substituted aldehydes allows to graft various functionalized groups on the lateral chain of the amino acid, such as trifluoromethyl, cyano, nitro, ferrocenyl, boronato, or azido. In addition, the reaction of the amino acid Wittig reagent with α,β-unsaturated aldehydes leads to amino acids bearing a diene on the lateral chain. Finally, this amino acid phosphonium salt appears to be a new powerful tool for the preparation of unsaturated and non-proteinogenic α-amino acids, directly usable for the synthesis of customized peptides.

The synthesis of a chiral β-amino acid derivative by the Grignard reaction of an aspartic acid equivalent

A novel synthetic route to chiral β-amino acid derivative has been developed by a Grignard reaction of 2,4,5-trifluo- rophenyl magnesium bromide with the Weinreb amide derivative of L-aspartic acid. The aspartic equivalent was synthesised from L-aspartic