Name: 1-BOC-Azetidine-3-carboxylic acid methyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Methyl 1-Boc-azetidine-3-carboxylate; 1-tert-butyl 3-methyl azetidine-1,3-dicarboxylate

IUPAC Name

1-O-tert-butyl 3-O-methyl azetidine-1,3-dicarboxylate

Canonical SMILES

CC(C)(C)OC(=O)N1CC(C1)C(=O)OC

InChI

InChI=1S/C10H17NO4/c1-10(2,3)15-9(13)11-5-7(6-11)8(12)14-4/h7H,5-6H2,1-4H3

InChIKey

SECFRXGVLMVUPD-UHFFFAOYSA-N

Density

1.2±0.1 g/cm3

Boiling Point

269.0±33.0 °C at 760 mmHg

1-BOC-Azetidine-3-carboxylic acid methyl ester, a widely utilized chemical intermediate in organic synthesis and drug development, possesses diverse applications. Here are four key applications articulated with heightened perplexity and burstiness:

Pharmaceutical Development: Playing a pivotal role in drug synthesis, this compound acts as a fundamental building block for an array of pharmaceuticals. Researchers harness its potential to innovate new medications by crafting intricate molecular architectures with tailored therapeutic actions. The protective BOC group it offers aids in orchestrating reaction pathways, ensuring the stability of intermediate compounds, and guiding the synthesis towards desired outcomes.

Peptide Synthesis: A cornerstone in peptide assembly, 1-BOC-Azetidine-3-carboxylic acid methyl ester functions as a strategic component in constructing peptide sequences as a shielded amino acid derivative. Its efficacy lies in fostering the formation of peptide bonds without interfering with other reactive sites within the molecule. This attribute renders it invaluable for assembling peptide chains with meticulous precision and unblemished purity, elevating the realm of peptide synthesis to new heights of precision and efficacy.

Medicinal Chemistry: Within the domain of medicinal chemistry, this compound serves as a potent tool for incorporating azetidine ring motifs into drug candidates. The introduction of azetidine moieties can significantly augment the pharmacokinetic and pharmacodynamic profiles of drugs, enhancing their potency and sustainability. This transformative alteration can pave the way for the development of novel therapeutic agents with heightened effectiveness and therapeutic potential, reshaping the landscape of medicinal chemistry through innovative pharmacological design.

Chemical Research: Proving indispensable in diverse chemical research pursuits, 1-BOC-Azetidine-3-carboxylic acid methyl ester is a catalyst for exploring reaction mechanisms and pioneering novel synthetic methodologies. Its distinct molecular structure empowers chemists to venture into uncharted territories of chemical reactions and transformations, driving forward the frontiers of synthetic organic chemistry and fostering a culture of innovation and discovery at the forefront of chemical research.

1.HMG-CoA reductase inhibitory activity and phytocomponent investigation of Basella alba leaf extract as a treatment for hypercholesterolemia.

Baskaran G1, Salvamani S1, Ahmad SA1, Shaharuddin NA1, Pattiram PD2, Shukor MY1. Drug Des Devel Ther. 2015 Jan 14;9:509-17. doi: 10.2147/DDDT.S75056. eCollection 2015.

The enzyme 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) reductase is the key enzyme of the mevalonate pathway that produces cholesterol. Inhibition of HMG-CoA reductase reduces cholesterol biosynthesis in the liver. Synthetic drugs, statins, are commonly used for the treatment of hypercholesterolemia. Due to the side effects of statins, natural HMG-CoA reductase inhibitors of plant origin are needed. In this study, 25 medicinal plant methanol extracts were screened for anti-HMG-CoA reductase activity. Basella alba leaf extract showed the highest inhibitory effect at about 74%. Thus, B. alba was examined in order to investigate its phytochemical components. Gas chromatography with tandem mass spectrometry and reversed phase high-performance liquid chromatography analysis revealed the presence of phenol 2,6-bis(1,1-dimethylethyl), 1-heptatriacotanol, oleic acid, eicosyl ester, naringin, apigenin, luteolin, ascorbic acid, and α-tocopherol, which have been reported to possess antihypercholesterolemic effects.

2.[GC-MS analysis of the fatty components of pollen Typhae before and after being carbonized].

Ma HF1, Liu B, Zhang GY, Shi RB, Ma CH, Yu MM. Zhongguo Zhong Yao Za Zhi. 2006 Feb;31(3):200-2.

OBJECTIVE: To study the changes of the fatty components of Pollen Typhae before and after being carbonized.