Effective Organotin-Mediated Regioselective Functionalization of Unprotected Carbohydrates

Yixuan Zhou, Kuo-Shiang Liao, Tzu-Yin Chen, Yves S Y Hsieh, Chi-Huey Wong

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Regioselective functionalization of unprotected carbohydrates at a secondary OH group in the presence of primary OH groups based on the commonly used organotin-mediated reaction has been improved. We found that the preactivation of the dibutylstannylene acetal intermediate with tetrabutylammonium bromide in toluene is a key to the improved condition for the efficient, high-yielding, and regioselective tosylation, benzoylation, or benzylation of unprotected carbohydrates. The counteranion of tetrabutylammonium ion with a weak coordination ability plays a crucial role in the improved regioselective reactions. A convenient access to the intermediates of synthetic value is also demonstrated in the organotin-mediated regioselective tosylation of unprotected carbohydrates, followed by the nucleophilic inversion reaction to give sulfur-containing and azide-modified carbohydrates.

Original languageEnglish
Pages (from-to)7141-7151
Number of pages11
JournalJournal of Organic Chemistry
Volume88
Issue number11
DOIs
Publication statusPublished - Jun 2 2023

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