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A Simple and Useful Synthetic Protocol for Selective Deprotection of tert ‐Butyldimethylsilyl (TBS) Ethers
Author(s) -
Khan Abu T.,
Ghosh Subrata,
Choudhury Lokman H.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400031
Subject(s) - chemistry , chemoselectivity , bromide , aryl , aqueous solution , organic chemistry , alkyl , aqueous medium , combinatorial chemistry , protecting group , catalysis , reaction conditions
A wide variety of tert ‐butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert ‐butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert ‐butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert ‐butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)