92886-86-7 | tert-Butyldiphenylsilyl Trifluoromethanesulfonate

CAS:92886-86-7 | tert-Butyldiphenylsilyl Trifluoromethanesulfonate ,Description

Tert-Butyldiphenylsilyl Trifluoromethanesulfonate (TBDPS-TFMS) is a reagent used in organic synthesis and a popular choice for organic chemists in their research. TBDPS-TFMS is a silylating agent, a type of reagent that can be used to introduce a silyl group into a molecule. Silylating agents are used to add a protective group to a molecule and protect it from unwanted reactions. TBDPS-TFMS is a versatile reagent that can be used in a variety of reactions, including the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 
 

Scientific Research Applications

Organocatalysis

tert-Butyldiphenylsilyl trifluoromethanesulfonate plays a significant role as a bifunctional organocatalyst. It is highly efficient in catalyzing asymmetric Michael addition reactions of ketones and aldehydes to nitrostyrenes. This process results in the synthesis of syn-selective adducts with exceptional yields, diastereoselectivities, and enantioselectivities (Wang, Yu, Liu, & Peng, 2009).

Protecting Group for Substituted Salicylic Acids

This compound is utilized in forming cyclic protecting groups for substituted salicylic acids. It efficiently reacts with a variety of electron-donating and withdrawing groups, leading to protected compounds in moderate to excellent yields (Pongdee, Bell, Prestwood, & Pongdee, 2020).

Stereoselective Alkylation

It is used in the α-alkylation of β-methyl-β-(tert-butyldiphenylsilyl)oxymethy-γ-butyrolactone enolates. This method facilitates the formation of consecutive quaternary and tertiary carbon centers with high diastereoselectivities (Uenishi, Tatsumi, Kobayashi, & Yonemitsu, 1995) .

Synthesis of Complex Organic Structures

It aids in the synthesis of complex organic structures, such as in the case of (+)-sesbanimide A. The protection of hydroxy groups in the synthesis process is a crucial step, where this compound unexpectedly led to the formation of a novel 2-O-silyl derivative with a tricyclic structure (Vloon, Bos, Willard, Koomen, & Pandit, 2010).

Multifunctional C-Phosphonio Phosphorus Vinyl Ylides Synthesis

This compound is integral in the synthesis of stable multifunctional C-phosphonio phosphorus vinyl ylides, showcasing its versatility in complex chemical syntheses (Dyer, Baceiredo, & Bertrand, 1996).

Hypervalent Phosphorus(III) Centers in Complexes

It reacts with multifunctional ligands to form Lewis acid-base complexes, highlighting its application in creating systems with hypervalent, low-coordinate phosphorus(III) centers (Burford, Phillips, Spinney, Lumsden, Werner‐Zwanziger, Ferguson, & McDonald, 2005).

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