154698-93-8

Usage

Uses

Used in Organic Synthesis:
2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide is used as a protective group for nitrogen-containing functional groups in organic chemistry reactions. The tert-butyldiphenylsilyl group serves as a protective group, allowing selective protection of amine functional groups during various synthetic processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide is used as a reagent for the synthesis of complex organic molecules, including drug candidates. Its ability to selectively protect amine functional groups enables the development of novel and effective pharmaceutical compounds.
Used in Chemical Research:
2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide is also utilized in chemical research for the study of reaction mechanisms and the development of new synthetic methodologies. Its selective protection of amine functional groups allows researchers to explore various reaction pathways and optimize synthetic routes for the preparation of target molecules.

Upstream product

• 76271-74-4 2-((t-butyldiphenylsilyl)oxy)acetic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 154698-92-7 methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 154698-94-9 (tert-Butyldiphenylsiloxy)methyl 2-<(methoxymethyl)oxy>-4-methylphenyl ketone 
• 158531-86-3 (tert-Butyldiphenylsiloxy)methyl 3,4-dimethoxyphenyl ketone 
• 159419-44-0 1-(tert-butyldiphenylsiloxy)hex-5-en-2-one 
• 200571-96-6 (E)-1-(tert-Butyl-diphenyl-silanyloxy)-7,7-dimethoxy-4-methyl-hept-3-en-2-one 
• 204916-61-0 1-(tert-butyl-diphenyl-silanyloxy)-but-3-en-2-one 
• 193292-63-6 7-[(tert-butyldimethylsilyl)oxy]-1-[(tert-butyldiphenylsilyl)oxy]-3-heptyn-2-one 
• 335455-42-0 (3E,8Z,10Z)-10-(tert-Butyl-diphenyl-silanyloxymethyl)-8-methyl-dodeca-3,8,10-trien-2-one 
• 1278444-56-6 (R)-1-(tert-butyldiphenylsilyloxy)pent-3-yn-2-ol 
• 193292-65-8 1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 

Relevant academic research and scientific papers

An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter.

Highly enantiopure (tert-butyldiphenylsilyloxymethyl)oxiranes from barium carbonate

The synthesis of (2R)-(tert-butyldiphenylsilyloxymethyl)oxirane and the (2S)-enantiomer from barium carbonate was developed. Methyl glycolate or the hydroxamate analog was prepared and in turn reacted with (S)-(-)-methyl p- tolylsulfoxide or the (R)-enantiomer to make β-keto sulfoxides. From the sulfoxides, we made the diastereoisomeric alcohols in a highly selective sulfoxide group directed hydride reduction, and a Pummerer rearrangement reaction followed by deprotection yielded the enantiomeric diols. (2R)- (tert-Butyldiphenylsilyloxymethyl)oxirane and its (2S)-enantiomer were derived from these diols in an overall yield of 56 % from barium carbonate. This method was developed to provide a convenient access to isotope-labeled analogs of these compounds.

A Remarkable Substituent Effect on the Enantioselectivity of Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols: A New Enantiocontrolled Synthesis of (-)-Debromoaplysin and (-)-Aplysin

A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2--2-cyclopropylideneethanol (18), affording (S)-(-)-2--2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed.This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework.