2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone
[CAS# 39968-95-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Lactone
• Name: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone
• Synonyms: (3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• Molecular Formula: C₁₄H₂₆O₄Si
• Molecular Weight: 286.44
• CAS Registry Number: 39968-95-1
• SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]([C@H]1CO)CC(=O)O2

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*, 1.07
• Index of Refraction: 1.485, Calc.^*
• Boiling Point: 376.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 181.5±23.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovery and Applications

2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone is a notable compound in organic chemistry, recognized for its unique structure and significant applications in synthetic organic processes. The discovery of this compound is part of ongoing research into the functionalization of lactones and their derivatives, which play critical roles in various synthetic pathways.

The synthesis of 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]corey lactone involves the protection of hydroxyl groups in lactones through silylation. The use of silyl protecting groups, such as the tert-butyldimethylsilyl (TBDMS) group, is a well-established strategy in organic synthesis to enhance the stability and reactivity of functional groups. The compound's synthetic pathway often employs chiral intermediates derived from lactones, leading to the formation of stereochemically enriched products.

One of the primary applications of 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]corey lactone is its role as a building block in the synthesis of complex natural products and pharmaceutical compounds. The lactone structure provides a versatile framework for further functionalization, allowing for the introduction of various functional groups through subsequent reactions. As a result, this compound is frequently utilized in the synthesis of bioactive molecules that exhibit therapeutic properties.

In addition to its applications in medicinal chemistry, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]corey lactone is also of interest in materials science. Its ability to form stable siloxane bonds makes it a candidate for use in the development of silicone-based materials, which have a wide range of applications, including sealants, adhesives, and coatings. The incorporation of the corey lactone moiety can enhance the properties of these materials, providing unique characteristics such as increased thermal stability and improved mechanical performance.

Furthermore, the compound serves as a valuable intermediate in the study of reaction mechanisms and stereochemical outcomes in organic synthesis. By investigating the reactivity of silylated lactones, chemists can gain insights into the fundamental principles governing chemical reactions, contributing to the development of new synthetic methodologies.

In summary, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]corey lactone is a significant compound in the field of organic chemistry, with diverse applications ranging from medicinal chemistry to materials science. Its unique structure and reactivity make it a valuable building block for the synthesis of complex organic molecules, reinforcing its importance in both academic research and industrial applications.

References

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