Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides
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- Self-Promoted Glycosylation for the Synthesis of β-N-Glycosyl Sulfonyl Amides_(accepted_version)
Accepted author manuscript, 1.39 MB, PDF document
N-Glycosyl N-sulfonyl amides have been synthesized by a self-promoted glycosylation, i.e. without any catalysts, promotors or additives. When the reactions were carried out at lower temperatures a mixture of N- and O-glycosides were observed, where the latter rearranged to give the β-N-glycosides at elevated temperatures. By this method sulfonylated asparagine derivatives can be selectively β-glycosylated in high yields by trichloroacetimidate glycosyl donors of different reactivity including protected glucosamine derivatives. The chemoselectivity in the glycosylations as well as the rearrangements from O-glycosides to β-N-glycosides gives information of the glycosylation mechanism. This method gives access to glycosyl sulfonyl amides under mild conditions.
Original language | English |
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Journal | European Journal of Organic Chemistry |
Volume | 2021 |
Issue number | 41 |
Pages (from-to) | 5685-5689 |
Number of pages | 5 |
ISSN | 1099-0690 |
DOIs | |
Publication status | Published - 2021 |
- Asparagine, Chemoselectivity, diastereoselectivity, N-Glycosylation, Self-promoted
Research areas
ID: 276273890