L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride
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L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-004123
CAS number
218938-66-0
Molecular Formula
C11H19NO4·HCl
Molecular Weight
265.76
L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride
IUPAC Name
4-O-tert-butyl 1-O-prop-2-enyl (2S)-2-aminobutanedioate;hydrochloride
Synonyms
L-Asp(OtBu)-OAll HCl; H-Asp(OtBu)-allyl ester; H-ASP(OTBU)-ALLYL ESTER HCl; H-ASP(OTBU)-OAL HCl
Appearance
Yellow solid
Purity
≥ 98% (NMR)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H19NO4.ClH/c1-5-6-15-10(14)8(12)7-9(13)16-11(2,3)4;/h5,8H,1,6-7,12H2,2-4H3;1H/t8-;/m0./s1
InChI Key
NJRAKVZUBAZRJQ-QRPNPIFTSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)OCC=C)N.Cl

L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride is a chemical compound that plays a significant role in organic synthesis and pharmaceutical development. It is derived from L-Aspartic acid, a naturally occurring amino acid, and is modified through esterification to enhance its utility in various applications. The compound is characterized by the presence of two ester groups, a tert-butyl ester and an allyl ester, which contribute to its unique reactivity and functional properties. The hydrochloride part of the compound indicates it is in the form of a hydrochloride salt, enhancing its solubility and stability which are key considerations for its use in industrial and laboratory settings.

One of the primary applications of L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride is in the field of pharmaceuticals, particularly as an intermediate in the synthesis of active pharmaceutical ingredients (APIs). Its esters provide reactive sites that can be selectively manipulated to introduce various functional groups, making it indispensable in creating complex molecular architectures. This adaptability is crucial for the development of new drugs, where precise modifications at the molecular level can significantly affect the efficacy and safety profile of a medication. By facilitating the synthesis of diverse chemical structures, this compound plays a vital role in drug discovery and development.

Another key application area is in the field of peptide synthesis. Peptides, which are short chains of amino acids, have garnered significant interest due to their therapeutic potential and role in biological systems. L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride serves as a protected amino acid, allowing for controlled peptide bond formation. The protective ester groups prevent undesirable side reactions during the synthesis process, thereby enabling the efficient assembly of target peptides. This aspect is particularly beneficial in synthesizing complex peptides used in research and therapeutic applications, ensuring high purity and yield.

The compound also finds use in the development of novel materials, particularly in polymers and resins. The reactive ester groups facilitate polymerization processes, allowing for the creation of materials with specific properties such as enhanced durability, flexibility, and thermal stability. This capability is advantageous in designing materials for specialized applications, including biomedical devices, coatings, and adhesives. The introduction of functional groups through ester modification can impart desired characteristics to the polymers, enhancing their applicability in diverse industrial sectors.

Finally, L-Aspartic acid β-tert-butyl ester α-allyl ester hydrochloride is utilized in research as a versatile reagent for structural and mechanistic studies in chemistry. Its ability to undergo selective reactions makes it an excellent model compound for exploring reaction pathways and mechanisms. Researchers can utilize it to study the effects of different catalytic conditions, reaction environments, and substitution patterns on reaction outcomes. This knowledge not only advances the field of organic chemistry but also assists in the development of greener and more efficient synthetic methods, ultimately contributing to more sustainable practices in chemical manufacturing.

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