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Synlett 2011(6): 821-825  
DOI: 10.1055/s-0030-1259917
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium

Mahagundappa R. Maddani, Kandikere R. Prabhu*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Fax: +91(80)23600529; e-Mail: prabhu@orgchem.iisc.ernet.in;
Further Information

Publication History

Received 3 January 2011
Publication Date:
16 March 2011 (online)

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Abstract

Employing aqueous tert-butyl hydroperoxide (70%) as an inexpensive reagent a useful methodology for the regioselective and chemoselective deprotection of terminal acetonide groups in aqueous medium is developed. A variety of acetonide derivatives on reaction with aqueous tert-butyl hydroperoxide in water:tert-­butanol (1:1) furnish the corresponding acetonide deprotected diols in good yields. A large number of acid labile protecting functional groups and other functional moieties were found to be unaffected under the conditions employed for the present deprotection. This method has been successfully applied to sugar derivatives.

Key words

deprotection - acetonide - tert-butyl hydroperoxide - chemoselectivity - protecting group - diols

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28

It was anticipated that the lactol would be oxidized to the corresponding lactone (2b) under the present reaction conditions. Contrary to our expectation, although the lactol has disappeared during the reaction, the corresponding lactone 2b was not observed.

29

Yield based on the recovery of unreacted starting material 4 (10%).

31

Yield based on the recovery of the unreacted starting material 11 (25%).