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- Title
Self‐Promoted Glycosylation for the Synthesis of β‐N‐Glycosyl Sulfonyl Amides.
- Authors
Mała, Patrycja; Pedersen, Christian Marcus
- Abstract
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.
- Subjects
GLYCOSYLATION; AMIDES; HIGH temperatures; SULFONYL compounds; ASPARAGINE; CHEMOSELECTIVITY
- Publication
European Journal of Organic Chemistry, 2021, Vol 2021, Issue 41, p5685
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202100808