215807-84-4

Basic information

• Product Name: 1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-one
• Synonyms: 1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-one
• CAS NO: 215807-84-4
• Molecular Weight: 450.674
• Mol File: 215807-84-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-one(215807-84-4)
• EPA Substance Registry System: 1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-one(215807-84-4)

Safety Data

• Hazardous Substances Data: 215807-84-4(Hazardous Substances Data)

Upstream product

• 5056-07-5 (S)-methyl p-tolyl sulfoxide 
• 154698-92-7 methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate 

Downstream Products

• 161469-43-8 (S)-3-((tert-butyldiphenylsilyl)oxy)propane-1,2-diol 
• 106731-74-2 tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane 
• 215807-86-6 (R)-1-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-toluene-4-sulfinyl)-propan-2-ol 

Relevant articles and documents

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.