Facile cleavage of triethylsilyl (TES) ethers using o-lodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2141-2144

  Wu, Yikang ^a   Huang, Jia Hui ^a   Shen, Xin ^a   Hu, Qi ^a   Tang, Chao Jun ^a   Li, Liang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODYLBENZOIC ACID; 2-IODOXYBENZOIC ACID; BIOLOGICAL FACTOR; DRUG DERIVATIVE; ETHER DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; ORGANOSILICON DERIVATIVE; PEPTIDE; T BUTYLDIMETHYLSILYL COMPOUNDS; T-BUTYLDIMETHYLSILYL COMPOUNDS; TESTOLACTONE; TROMETAMOL;

ARTICLE; BIOMEDICINE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; SYNTHESIS;

BIOLOGICAL FACTORS; BIOLOGICAL SCIENCES; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHERS; IODOBENZOATES; ORGANOSILICON COMPOUNDS; PEPTIDES; TROMETHAMINE;

EID: 0037182709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025946n     Document Type: Article

References (22)

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17. 4. The solvents were removed by rotary evaporation, and the products were obtained by flash chromatography on silica gel (eluting with ethyl acetate/hexanes).
18. We chose this compund instead of structurely more closely related TBS ether 11 just for unambiguous identification of the origin of the alcohol in the product mixture.
19. It is noteworthy that Dess-Martin periodinane (structurally closely related to IBX) did not cleave TES while oxidizing alcohols into carbonyls. See, e.g.: Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017.
20. Tolstikov, G. A.; Miftakhov, M. S.; Vostrikov, N. S.; Komissarov, N. G.; Alder, M. E.; Kuznetsov, O. M. Zh. Org. Khim. 1988, 24, 224-225 (in Russian); Chem. Abstr. 1989, 110, 7162.
21. Tolstikov, G. A.; Miftakhov, M. S.; Vostrikov, N. S.; Komissarov, N. G.; Alder, M. E.; Kuznetsov, O. M. Zh. Org. Khim. 1988, 24, 224-225 (in Russian); Chem. Abstr. 1989, 110, 7162.
22. Note that most of the known cases (in moderate to good yields) of selective removal of TES without significantly touching TBS relied on hydrolysis in a mixture reaction medium of carefully tuned acidity. See, for example, those examples cited in ref 5.