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| LETTER | Synlett 2003: 0694-0698
DOI: 10.1055/s-2003-38360 |
© Georg Thieme Verlag Stuttgart ˙ New York
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A Highly Efficient and Useful
Synthetic Protocol for the Cleavage of tert-Butyldimethylsilyl
(TBS) Ethers Using a Catalytic Amount of Acetyl Chloride
in Dry Methanol
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| Abu T. Khan*, Ejabul Mondal |
Department of Chemistry, Indian Institute of Technology, North
Guwahati, Guwahati-781039, Assam, India
Fax: +91(361)2690762; e-Mail: atk@postmark.net;
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Received
21 January 2003 |
Abstract
A wide variety of tert-butyldimethylsilyl
(TBS) ethers as well as tert-butyldiphenylsilyl
(TBDPS) ethers 1 can be easily deprotected
to the corresponding parent hydroxyl compounds 2 by employing
catalytic amounts of acetyl chloride in dry MeOH at 0 °C
to room temperature in good yields. Some of the major advantages
are mild conditions, high efficiency, high selectivity, high yields,
easy operation, and also compatibility with other protecting groups.
Furthermore, no acetylation nor chlorination takes place under the
experimental conditions. Key words
deprotection - tert-butyldimethylsilyl
(TBS) ethers - tert-butyldiphenylsilyl
(TBDPS) ethers - acetyl chloride
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