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

Maddani, Mahagundappa R and Prabhu, Kandikere R (2011) Metal-Free Deprotection of Terminal Acetonides by Using tert-Butyl Hydroperoxide in Aqueous Medium. In: Synlett (6). pp. 821-825.

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Official URL: https://www.thieme-connect.de/DOI/DOI?10.1055/s-00...

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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Thieme Medical Publishers.
Keywords: deprotection;acetonide;tert-butyl hydroperoxide; chemoselectivity;protecting group;diols
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 27 Apr 2011 05:25
Last Modified: 27 Apr 2011 05:25
URI: http://eprints.iisc.ernet.in/id/eprint/37142

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