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A nine-membered transition state characterizes the regioselective abstraction of the proton at C5′ that leads to the orthoacetate 2 as the product. The alkoxy radical intermediate is obtained from the Glc-α1→4-Glc derivative 1 with (diacetoxyiodo)benzene (DIB) and iodine. A similar 1,8-hydrogen abstraction results when the alkoxy radical intermediate is generated under reductive conditions.
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Francisco et al. (2002) studied this question.
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