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Synlett 1999; 1999(3): 311-312
DOI: 10.1055/s-1999-2606
DOI: 10.1055/s-1999-2606
letter
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Iodine and its Interhalogen Compounds: Versatile Reagents in Carbohydrate Chemistry IX. A Mild and Selective Deprotection of tert-Butyldimethylsilyl (TBDMS) Ethers in the Presence of Various Protecting Groups Using Iodine Monobromide
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Publication History
Publication Date:
31 December 1999 (online)
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Treatment of O-tert-butyldimethylsilyl (TBDMS) ethers of simple alcohols, carbohydrates or nucleosides with iodine monobromide in methanol or acetonitrile constitutes an effective method for their facile deprotection. The method can tolerate acid labile functionalities such as acetals, O-p-methoxybenzyl ethers, etc. as well as base labile groups such as esters and amides. An O-tert-butyldiphenylsilyl ether also survives the reaction conditions.
iodine monobromide - TBDMS ethers