Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers.
[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.
Wu
Yikang
Y
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
Huang
Jia-Hui
JH
Shen
Xin
X
Hu
Qi
Q
Tang
Chao-Jun
CJ
Li
Liang
L
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*
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