Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides

Ji Zhang, Niels R M Reintjens, Jayaraman Dhineshkumar, Martin D Witte*, Adriaan J Minnaard*

*Corresponding author for this work

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Abstract

To circumvent protecting groups, the site-selective modification of unprotected glycosides is intensively studied. We show that site-selective oxidation, followed by treatment of the corresponding trityl hydrazone with tert-butyl hypochlorite and a H atom donor provides an effective way to introduce a chloride substituent in a variety of mono- and disaccharides. The stereoselectivity can be steered, and a new geminal dichlorination reaction is described as well. This strategy challenges existing methods that lead to overchlorination.

Original languageEnglish
Number of pages6
JournalOrganic letters
DOIs
Publication statusE-pub ahead of print - 17-Jul-2022

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