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Comprehensive Guide to (1S,2R)-1-((Tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid (CAS No. 259214-55-6)

(1S,2R)-1-((Tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid (CAS No. 259214-55-6) is a highly specialized chiral cyclopropane derivative widely used in pharmaceutical synthesis and organic chemistry research. This compound features a unique vinylcyclopropane scaffold, which is increasingly sought after in drug discovery due to its ability to modulate biological activity and improve metabolic stability. The presence of the tert-butoxycarbonyl (Boc) protecting group enhances its utility in peptide coupling reactions, making it a valuable intermediate for peptide-based therapeutics.

In recent years, the demand for chiral building blocks like this compound has surged, driven by advancements in asymmetric synthesis and the growing focus on small-molecule drugs. Researchers are particularly interested in its potential applications for protein-protein interaction inhibitors and enzyme modulators. The vinyl group offers opportunities for further functionalization via click chemistry or cross-coupling reactions, aligning with trends in fragment-based drug design.

The compound's stereochemistry (1S,2R) is critical for its biological relevance, as enantiopure intermediates are essential for developing targeted therapies. Its cyclopropane ring contributes to conformational rigidity, a property leveraged in medicinal chemistry to enhance binding affinity. Analytical techniques such as HPLC and NMR are routinely employed to verify its purity and configuration, addressing the pharmaceutical industry's stringent quality standards.

From an industrial perspective, scalability is a key consideration. The synthesis of 259214-55-6 often involves transition metal-catalyzed cyclopropanation, a topic frequently searched in organic synthesis forums. Environmental sustainability is another hotspot, with researchers exploring green chemistry approaches to minimize waste during production. This aligns with the broader shift toward eco-friendly pharmaceutical manufacturing.

For those sourcing this compound, questions about storage conditions (typically -20°C under inert atmosphere) and solubility (compatible with DMSO, methanol, and dichloromethane) are common. Its role in peptide backbone modification and prodrug development further elevates its importance in bioconjugation strategies. As the field evolves, 259214-55-6 continues to attract attention for its versatility in structure-activity relationship (SAR) studies.

In summary, (1S,2R)-1-((Tert-Butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylic acid exemplifies the intersection of chiral technology and drug discovery. Its multifaceted applications—from peptide engineering to catalysis research—make it a cornerstone in modern synthetic chemistry. With the rise of AI-driven molecular design, compounds like this are poised to play pivotal roles in next-generation therapeutics.

• 159622-10-3((1R,2S)-1-(tert-Butoxycarbonyl)amino-2-vinylcyclopropanecarboxylic Acid)
• 259221-77-7((1R,2S)-1-(tert-Butoxycarbonylamino)-2-vinylcyclopropanecarboxylicacid)
• 915317-20-3(Cyclopropanecarboxylic acid,1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenyl-, methyl ester,(1R,2R)-)
• 88950-67-8(Cyclopropanecarboxylic acid,1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-(1-methylethyl)-, trans-)
• 136378-33-1((1S,2S)-1-[(Tert-Butoxycarbonyl)amino]-2-methylcyclopropane-1-carboxylic acid)
• 1001667-24-8(2-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylic Acid)
• 213316-50-8(cis-1-(tert-butoxycarbonylamino)-2-vinyl-cyclopropanecarboxylic acid)
• 159622-09-0(methyl (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinyl-cyclopropanecarboxylate)
• 88950-66-7(rac-(1R,2R)-1-{(tert-butoxy)carbonylamino}-2-ethylcyclopropane-1-carboxylic acid, cis)
• 88950-65-6((1S,2S)-1-(tert-butoxycarbonylamino)-2-methyl-cyclopropanecarboxylic acid)