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

K. P. Ravindranathan Kartha; Robert A. Field

doi:10.1055/s-1999-2606

Synlett 1999; 1999(3): 311-312
DOI: 10.1055/s-1999-2606

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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

K. P. Ravindranathan Kartha^* , Robert A. Field

^*School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, U.K.; Fax +44 (13 34) 46 38 08

Abstract

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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

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