22396-22-1

Usage

Derivative of

Octadecanoic acid (Stearic acid)

Added groups

Trimethylsilyloxy group and trimethylsilyl ester group

Function

Protecting group for carboxylic acids in organic synthesis

Allows

Selective reactions to take place while protecting the carboxylic acid functionality

Used as

Precursor for the synthesis of various types of lipids and other organic compounds

Applications

Important in organic chemistry

Utility

Useful tool for chemical synthesis

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 106-14-9 12-Hydroxystearic acid 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 

Relevant academic research and scientific papers

Hydrogen and trimethylsilyl transfers during EI mass spectral fragmentation of hydroxycarboxylic and oxocarboxylic acid trimethylsilyl derivatives

This paper, describing electron ionization mass spectral fragmentation of some hydroxycarboxylic and oxocarboxylic acid trimethylsilyl derivatives, focuses on the formation of fragment ions resulting from the interactions between the two functionalities of these compounds. These interactions result in the formation of fragment ions at [CH2=C(OTMS)2]+·, [CH2=CHC(OTMS)=OTMS]+, [M-31]+, [M-105]+, and [M-RCHO]+· in the case of hydroxycarboxylic acid trimethylsilyl derivatives of formula RCHOTMS(CH2)nCOOTMS and at [RC(OTMS)=CH2]+·, [RC(=OTMS)CH=CH2]+, and [M - RC(=O)CH2]+ in the case of oxocarboxylic acid trimethylsilyl esters of formula RC(=O)(CH2)nCOOTMS. Some of these fragmentations appeared to be sufficiently specific to be used to characterize these compounds. Several fragmentation pathways involving trimethylsilyl and hydrogen transfers were proposed to explain the formation of these different fragment ions and were substantiated by deuterium labeling.

Facile Synthesis of Lactones from Silyl ω-Siloxycarboxylates Using p-Trifluoromethylbenzoic Anhydride and a Catalytic Amount of Active Lewis Acid

The lactonization of silyl ω-siloxycarboxylates is successfully carried out under mild conditions in good to high yields by using p-trifluoromethylbenzoic anhydride and a catalytic amount of active acidic species generated in situ from TiCl4 and AgClO4.