1443780-14-0

Basic information

• Product Name: (E)-3-(tert-butyldimethylsilyl)-1-tosylallyl diisopropylcarbamate
• Synonyms: (E)-3-(tert-butyldimethylsilyl)-1-tosylallyl diisopropylcarbamate
• CAS NO: 1443780-14-0
• Molecular Weight: 453.718
• Mol File: 1443780-14-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-3-(tert-butyldimethylsilyl)-1-tosylallyl diisopropylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(tert-butyldimethylsilyl)-1-tosylallyl diisopropylcarbamate(1443780-14-0)
• EPA Substance Registry System: (E)-3-(tert-butyldimethylsilyl)-1-tosylallyl diisopropylcarbamate(1443780-14-0)

Safety Data

• Hazardous Substances Data: 1443780-14-0(Hazardous Substances Data)

Upstream product

• 122539-65-5 (E)-3-[(tert-butyl)dimethylsilyl]prop-2-en-1-ol 
• 19009-39-3 N,N-diisopropylcarbamoyl chloride 
• 455-16-3 p-toluenesulfonyl fluoride 
• 1443780-03-7 (E)-3-(tert-butyldimethylsilyl)allyl diisopropylcarbamate 

Downstream Products

• 1443780-15-1 3-(tert-butyldimethylsilyl)-2,3-dihydroxy-1-tosylpropyl diisopropylcarbamate 
• 1443780-16-2 (5-(tert-butyldimethylsilyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(tosyl)methyl diisopropylcarbamate 
• 1443780-17-3 C₂₃H₃₉NO₅SSi 

Relevant articles and documents

Chirality transfer in Brook rearrangement-mediated SE2′ solvolytic protonation and its use in estimation of the propensity for racemization of the α-lithiocarbanions of the substituents

Chirality transfer from an α-silylalcohol to α-carbmoyloxy- and α-siloxyallyl-carbanions was investigated using a Brook rearrangement-mediated SE2′ protonation in γ- carbamoyloxy- and γ-siloxy-α-silylallyl alcohols. We proposed a hypothesis that the reaction proceeds along one of two pathways that involves (1) a concerted protonation of a silicate intermediate and (2) a concerted lithiation of the intermediate followed by protonation with retention or by protonation after racemization. Comparison of the extent of the chirality transfer provides a new method for semi-quantitative evaluation of the propensity for racemization of lithiocarbanions next to a conjugative electron-withdrawing group.