86032-05-5Relevant academic research and scientific papers
Samarium trifluoromethanesulfonate: An efficient moisture tolerant acylation catalyst under solvent-free condition
Roy, Bimalendu,Dasgupta, Somnath,Kumar Rajput, Vishal,Mukhopadhyay, Balaram
, p. 1 - 9 (2008/09/21)
Samarium trifluoromethanesulfonate catalyzed the acylation of phenols, alcohols, thiols, free reducing sugars, and glycosides in excellent yields at ambient temperature under solvent-free condition using stoichiometric amounts of various anhydrides. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.
COMPETITIVE FORMATION OF PERACETYLATED α-L-ARABINOPYRANOSIDES AND β-L-ARABINOPYRANOSE 1,2-(ALKYL ORTHOACETATES) IN KOENIGS-KNORR-CONDENSATIONS
Magnus, Volker,Vikich-Topich, Drazen,Iskrich, Sonja,Kveder, Sergije
, p. 209 - 224 (2007/10/02)
Mixtures of peracetylated β-L-arabinopyranose 1,2-(alkyl-orthoacetates) and the corresponding α-L-arabinopyranosides, in ratioa as high as 1:1.3, have been obtained from primary, secondary, and tertiary alcohols and 2,3,4-tri-O-acetyl-β-L-arabinosyl bromide, by reaction in dichloromethane-diethyl ether (3:1) in the presence of silver oxide and anhydrous calcium sulfate.Orthoester formation decreased when dichloromethane was replaced by the less-polar chloroform or carbon tetrachloride, and also when diethyl ether was replaced by the more bulky dibutyl or di-isopropyl ethers.The product distribution, which is unusual for Koenigs-Knorr condensations involving 1,2-cis acylglycosyl halides in the presence of silver oxide, may be ascribed to competitive inhibition of glycoside formation by complexation of the intermediate glycosyl cation with ether and to solvent polarity effects.
