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α-Selective Glucosylation Can Be Achieved with 6- O- para-Nitrobenzoyl Protection

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A systematic study of the effect of various 6-O-acyl groups on anomeric selectivity in glucosylations with thioglycoside donors was conducted. All eight different esters were found to induce moderate-to-high α-selectivity in glucosylation with l-menthol with the best being 6-O-p-nitrobenzoyl. The effect appears to be general across various glucosyl acceptors, glucosyl donor types, and modes of activation. No evidence was found in favor of distal participation.

Original languageEnglish
JournalJournal of Organic Chemistry
Pages (from-to)13763-13789
Number of pages27
Publication statusPublished - Nov 2022

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