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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

(2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid (CAS No. 109523-13-9)

(2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid (CAS No. 109523-13-9) is a versatile compound with significant applications in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of indole derivatives and is characterized by its unique stereochemistry and functional groups, making it an important building block in the synthesis of various bioactive molecules.

The chemical structure of (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid consists of an indole core with a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom and a carboxylic acid group at the C-2 position. The presence of these functional groups allows for a wide range of chemical transformations and derivatizations, which are crucial in the development of novel therapeutic agents.

Recent studies have highlighted the importance of (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid in the synthesis of peptidomimetics and small molecule inhibitors. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated that this compound serves as a key intermediate in the synthesis of potent inhibitors targeting protein-protein interactions (PPIs). These inhibitors have shown promising results in preclinical studies for treating various diseases, including cancer and neurodegenerative disorders.

In addition to its role in PPI inhibitors, (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid has also been utilized in the development of peptidomimetics for modulating G protein-coupled receptors (GPCRs). GPCRs are a large family of membrane receptors that play critical roles in cellular signaling pathways. A recent study published in Bioorganic & Medicinal Chemistry Letters reported the synthesis of GPCR modulators using this compound as a key building block. These modulators exhibited high selectivity and potency, making them potential candidates for drug development.

The stereochemistry of (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid is another factor that contributes to its utility in medicinal chemistry. The specific stereoconfiguration at the C-2 position ensures that the resulting derivatives have optimal biological activity and pharmacokinetic properties. This is particularly important in the design of drugs that require high selectivity and minimal side effects.

The synthetic accessibility of (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid has been extensively studied. Various synthetic routes have been developed to efficiently produce this compound on both laboratory and industrial scales. One notable method involves the use of asymmetric catalysis to achieve high enantioselectivity and yield. This approach not only simplifies the synthetic process but also reduces the environmental impact by minimizing waste generation.

In terms of its physical and chemical properties, (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl]-octahydro-1H-indole-2-carboxylic acid is a white crystalline solid with a melting point ranging from 85°C to 87°C. It is soluble in common organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO), making it suitable for various chemical reactions and analytical techniques. The compound is stable under standard laboratory conditions but should be stored away from strong acids and bases to prevent degradation.

The safety profile of (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl)-octahydro-1H-indole-2-carboxylic acid has been evaluated through extensive toxicological studies. These studies have shown that the compound is generally safe for use in laboratory settings when appropriate safety protocols are followed. However, it is important to handle this compound with care to avoid inhalation or skin contact.

In conclusion, (2S,3aS,7aS)-1-[(tert-butoxy)carbonyl)-octahydro-1H-indole-2-carboxylic acid (CAS No. 109523-13-9) is a valuable compound with diverse applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure and stereochemistry make it an ideal building block for synthesizing bioactive molecules with potential therapeutic applications. Ongoing research continues to explore new avenues for utilizing this compound in drug discovery and development.

• 45170-31-8((2S)-2-[[(tert-Butoxy)carbonyl](methyl)amino]-3-methylbutanoic acid)
• 37784-17-1(N-Boc-D-proline)
• 13139-16-7(Boc-L-Ile-OH)
• 13726-69-7(Boc-Hyp-OH)
• 15761-39-4(Boc-L-Pro-OH)
• 59936-29-7(1-tert-butyl 2-methyl (2S)-pyrrolidine-1,2-dicarboxylate)
• 84348-37-8((2S)-1-tert-butoxycarbonyl-4-oxo-pyrrolidine-2-carboxylic acid)
• 70491-05-3(Boc-D-Chg-OH)
• 73323-65-6(1-tert-butyl 2-methyl (2R)-pyrrolidine-1,2-dicarboxylate)
• 51077-14-6((2S)-1-[(tert-butoxy)carbonyl]azetidine-2-carboxylic acid)