359867-66-6

Basic information

• Product Name: tert-butyl(cyclohexa-2,4-dien-1-ylmethoxy)dimethylsilane
• Synonyms: tert-butyl(cyclohexa-2,4-dien-1-ylmethoxy)dimethylsilane
• CAS NO: 359867-66-6
• Molecular Weight: 224.418
• Mol File: 359867-66-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl(cyclohexa-2,4-dien-1-ylmethoxy)dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl(cyclohexa-2,4-dien-1-ylmethoxy)dimethylsilane(359867-66-6)
• EPA Substance Registry System: tert-butyl(cyclohexa-2,4-dien-1-ylmethoxy)dimethylsilane(359867-66-6)

Safety Data

• Hazardous Substances Data: 359867-66-6(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 930-68-7 cyclohexenone 
• 832131-69-8 (+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol 
• 290355-85-0 4-(tert-butyldimethylsilyloxymethyl)-cyclohex-1-ene 
• 72581-32-9 cyclohex-3-enylmethanol 
• 145386-69-2 6-[(tert-butyldimethylsilyloxy)methyl]-1-trimethylsilyloxy-1-cyclohexene 
• 140139-05-5 bromomethoxy(t-butyl)dimethylsilane 
• 135297-11-9 C₁₃H₂₆O₂Si 

Downstream Products

• 87905-98-4 5-<(benzyloxycarbonyl)amino>pentanol 
• 359867-76-8 {(R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-3-hydroxy-pentyl}-carbamic acid cyclohexa-2,4-dienylmethyl ester 
• 359867-75-7 Acetic acid (R)-1-(2-acetoxy-ethyl)-3-(cyclohexa-2,4-dienylmethoxycarbonylamino)-propyl ester 
• 359867-74-6 imidazole-1-carboxylic acid cyclohexa-2,4-dienylmethyl ester 
• 154916-94-6 5-(hydroxymethyl)-1,3-cyclohexadiene 

Relevant articles and documents

Maleimide-based metal-free ligation with dienes: A comparative study

A brief literature survey reveals that metal-free ligation such as the maleimide-based cycloaddition with electron-rich (hetero)dienes is a widespread tool for the assembly of (bio)molecular systems with applications in biotechnology, materials science, polymers and bio-organic chemistry. Despite their everyday use, only scattered data about their kinetics as well as the stabilities of corresponding products under physiological conditions, are accessible. These key parameters are yet, of paramount importance to ensure the rapid and effective preparation of stable compounds. Herein is reported a systematic study regarding the different classes of dienes used in chemoselective ligation, including their accessibility and stability, as well as comparative kinetic experiments and products stability assays. We took advantage of these data to develop a double labeling strategy from the combined use of cyclopentadiene and oxazole dienes.

Diels-Alder bioconjugation of diene-modified oligonucleotides

In an effort to offer complementary technology for covalent biomolecule modification (bioconjugation), we have developed a method that exploits the aqueous acceleration of Diels-Alder reactions for this purpose. Three different diene phosphoramidite reagents have been synthesized that enable diene modification of synthetic oligonucleotides prepared by the phosphoramidite method. Clean and efficient Diels-Alder cycloaddition of these diene oligonucleotides with maleimide dieneophiles was carried out, and the labeled oligonucleotide bioconjugates were characterized by HPLC and electrospray mass spectrometry. Dieneophile stoichiometry, temperature, and pH are all parameters that were shown to influence the efficiency of the process.