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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