Abstract
The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2′,6′-di- O-benzyl-2,3:3′,4′-di- O-isopropylidenelactose dimethyl acetal ( 1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups.
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