title: Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers.
abstract: [reaction: see text] In DMSO cleavage of triethylsilyl (TES) ethers by o-iodoxybenzoic acid (IBX) was significantly faster than cleavage of tert-butyldimethylsilyl (TBS) ethers or further oxidation into carbonyl compounds. In most cases, TES protecting groups could be removed in good to excellent yields within 1 h, whereas similar TBS protecting groups remained intact under the same conditions. The procedure also could be adapted for direct one-pot conversion of TES ethers into carbonyl compounds.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. yikangwu@pub.sioc.ac.cn
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu
authors.forename: Jia-Hui
authors.initials: JH
authors.lastname: Huang
authors.forename: Xin
authors.initials: X
authors.lastname: Shen
authors.forename: Qi
authors.initials: Q
authors.lastname: Hu
authors.forename: Chao-Jun
authors.initials: CJ
authors.lastname: Tang
authors.forename: Liang
authors.initials: L
authors.lastname: Li
mesh_terms: D001685:Biological Factors / Q000138:chemical synthesis; D001690:Biological Science Disciplines / Q000379:methods; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D004987:Ethers / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis; D014325:Tromethamine / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D001685:Biological Factors; D004987:Ethers; D007462:Iodobenzenes; D007463:Iodobenzoates; D017646:Organosilicon Compounds; D010455:Peptides; C009660:t-butyldimethylsilyl compounds; D014325:Tromethamine; C476101:o-iodoxybenzoic acid; C004551:TES