-CHEMOSELECTIVITY AND DEPROTECTION-

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Leading Question: Provide a brief explanation for the observed chemoselectivity for the deprotection of the two hydroxy-protecting groups.

The carbon-oxygen bond has a higher electron density (that is, it is more electronegative) than the silicon-oxygen bond. Since DDQ is an electron sink, it will then deprotect the carbon-oxygen first to provide the chemioselective product. The cleavage of the PMB instead of the TBDPS deprotection group will occur because, under oxidative conditions, the DDQ’s electrons will be more attracted towards the C-O bond.

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