tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate
[CAS# 1252686-29-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate
• Synonyms: tert-butyl N-[(2S)-1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl]carbamate
• Protein Sequence: X
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.37
• CAS Registry Number: 1252686-29-5
• SMILES: CCOC1=CC=C(C=C1)C[C@@H](CO)NC(=O)OC(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.513, Calc.^*
• Boiling Point: 455.4±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 229.2±27.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

Tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate is a chemical compound with growing significance in the pharmaceutical and chemical research sectors. Its discovery is tied to advancements in asymmetric synthesis and the design of chiral molecules, which are crucial in the development of drugs with specific biological activity. This compound is particularly interesting due to its chiral nature, which plays a vital role in its functionality and effectiveness in various applications.

The synthesis of tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate involves the reaction between a chiral precursor and a carbamoylating agent, leading to the formation of the desired product with high enantiomeric purity. The stereochemistry of the compound is crucial, as it influences the interaction with biological targets, making the (S)-enantiomer particularly important in medicinal chemistry.

One of the primary applications of tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate is in the development of pharmaceuticals, where it serves as a building block for the synthesis of drugs that target specific receptors in the body. Its structure allows for the modification of the molecule to enhance its pharmacokinetic properties, such as solubility, bioavailability, and metabolic stability. Additionally, the compound's ability to form hydrogen bonds through its hydroxyl and carbamate groups makes it a versatile intermediate in drug design, enabling the creation of molecules with optimal binding affinities to biological targets.

In the context of drug discovery, the (S)-enantiomer of tert-butyl (1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate has shown promise in preclinical studies for the treatment of various conditions, including neurological disorders and cancer. Its ability to modulate specific biological pathways through chiral recognition highlights the importance of enantiomeric purity in drug efficacy and safety. Furthermore, this compound is also utilized in the synthesis of prodrugs, where it can be metabolized in vivo to release the active drug in a controlled manner, improving the therapeutic index and reducing side effects.

The synthesis and application of tert-butyl (S)-(1-(4-ethoxyphenyl)-3-hydroxypropan-2-yl)carbamate demonstrate the significance of chiral molecules in modern chemistry. The development of efficient synthetic routes to produce this compound with high enantiomeric purity has been a key achievement, enabling its use in various pharmaceutical applications. As research continues, the potential of this compound to contribute to the development of new and more effective therapies remains a promising area of study.