Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides.
A simple and efficient method is developed for the chemoselective one-pot conversion of ethers (benzyl, TBDMS and acetal) to the corresponding benzoates by zinc triflate-catalyzed deprotection and benzoylation by benzoyl bromide. In the same reaction, methyl or p-methoxyphenyl glycosides are converted into glycosyl bromides that are useful in glycosylation reactions.
Polat
Tülay
T
Department of Chemistry, The University of Iowa, 52242, Iowa City, IA, USA.
Linhardt
Robert J
RJ
D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry*; D004986:Ether / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*
D001565:Benzoates; D008698:Mesylates; D004986:Ether; C009852:benzoyl bromide; C012077:trifluoromethanesulfonic acid