79271-56-0 | Triethylsilyl trifluoromethanesulfonate

Packsize	Purity	Availability	Price	Discounted Price
25g	98%	in stock	$25.00	$18.00

Description

• Catalog Number: AB80024
• Chemical Name: Triethylsilyl trifluoromethanesulfonate
• CAS Number: 79271-56-0
• Molecular Formula: C7H15F3O3SSi
• Molecular Weight: 264.3379
• MDL Number: MFCD00000407
• SMILES: CC[Si](OS(=O)(=O)C(F)(F)F)(CC)CC

Computed Properties

• Complexity: 281
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5

Upstream Synthesis Route

Triethylsilyl trifluoromethanesulfonate, commonly referred to as TESOTf, is a versatile and highly efficient reagent used in various chemical synthesis applications. This powerful silylating agent is particularly valued for its ability to introduce trimethylsilyl (TMS) groups to a wide range of functional groups, making it a crucial tool in organic synthesis.One of the primary applications of Triethylsilyl trifluoromethanesulfonate is in the protection of hydroxyl groups in organic molecules. By selectively silylating hydroxyl groups using TESOTf, chemists can mask these reactive functionalities during complex reactions, thereby preventing unwanted side reactions and ensuring the desired outcome in multistep synthesis processes. This protection strategy is essential in the synthesis of pharmaceuticals, natural products, and other complex organic compounds.Additionally, Triethylsilyl trifluoromethanesulfonate is utilized in the installation of silyl enol ethers, which serve as versatile intermediates in various organic transformations such as aldol condensations, Michael additions, and Wittig reactions. The high reactivity of TESOTf towards enolizable carbonyl compounds allows for efficient and selective formation of silyl enol ethers, enabling chemists to access diverse synthetic pathways towards desired target molecules.In summary, Triethylsilyl trifluoromethanesulfonate plays a crucial role in chemical synthesis by providing chemists with a powerful tool for selective functional group protection and versatile transformations. Its wide applicability and efficiency make it a valuable reagent in the synthetic chemist's toolkit, facilitating the development of novel molecules and compounds for various scientific and industrial purposes.

Literature

• Preparation of nucleosides derived from 2-nitroimidazole and D-arabinose, D-ribose, and D-galactose by the Vorbrüggen method and their conversion to potential precursors for tracers to image hypoxia.

  The Journal of organic chemistry 20111021