594-65-0Relevant articles and documents
Gilbert,E.E.
, p. 1801 - 1806 (1969)
Synthetic methodology towards allylic: Trans-cyclooctene-ethers enables modification of carbohydrates: Bioorthogonal manipulation of the lac repressor
Araman, Can,De Geus, Mark A. R.,Groenewold, G. J. Mirjam,Maurits, Elmer,Van Kasteren, Sander I.
, p. 10175 - 10179 (2020/10/13)
The inverse electron-demand Diels-Alder (IEDDA) pyridazine elimination is one of the key bioorthogonal bond-breaking reactions. In this reaction trans-cyclooctene (TCO) serves as a tetrazine responsive caging moiety for amines, carboxylic acids and alcohols. One issue to date has been the lack of synthetic methods towards TCO ethers from functionalized (aliphatic) alcohols, thereby restricting bioorthogonal utilization. Two novel reagents were developed to enable controlled formation of cis-cyclooctene (CCO) ethers, followed by optimized photochemical isomerization to obtain TCO ethers. The method was exemplified by the controlled bioorthogonal activation of the lac operon system in E. coli using a TCO-ether-modified carbohydrate inducer. This journal is
Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions
Wallach, Daniel R.,Chisholm, John D.
, p. 8035 - 8042 (2016/09/12)
An intermolecular alkylation of sulfonamides with trichloroacetimidates is reported. This transformation does not require an exogenous acid, base, or transition metal catalyst; instead the addition occurs in refluxing toluene without additives. The sulfonamide alkylation partner appears to be only limited by sterics, with unsubstituted sulfonamides providing better yields than more encumbered N-alkyl sulfonamides. The trichloroacetimidate alkylating agent must be a stable cation precursor for the substitution reaction to proceed under these conditions.
