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 language | English |
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Pages (from-to) | 5339-5344 |
Number of pages | 6 |
Journal | Organic letters |
Volume | 24 |
Issue number | 29 |
Early online date | 17-Jul-2022 |
DOIs | |
Publication status | Published - 29-Jul-2022 |
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CCDC 2150551: Experimental Crystal Structure Determination
Zhang, J. (Contributor), Reintjens, N. (Contributor), Jayaraman, D. (Contributor), Witte, M. D. (Contributor) & Minnaard, A. J. (Contributor), Cambridge Crystallographic Data Centre, 7-Feb-2022
DOI: 10.5517/ccdc.csd.cc2b5tmz
Dataset
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CCDC 2150550: Experimental Crystal Structure Determination
Zhang, J. (Contributor), Reintjens, N. (Contributor), Jayaraman, D. (Contributor), Witte, M. D. (Contributor) & Minnaard, A. J. (Contributor), Cambridge Crystallographic Data Centre, 7-Feb-2022
DOI: 10.5517/ccdc.csd.cc2b5tly
Dataset
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CCDC 2150508: Experimental Crystal Structure Determination
Zhang, J. (Contributor), Reintjens, N. (Contributor), Jayaraman, D. (Contributor), Witte, M. D. (Contributor) & Minnaard, A. J. (Contributor), Cambridge Crystallographic Data Centre, 7-Feb-2022
DOI: 10.5517/ccdc.csd.cc2b5s7k
Dataset