N‐Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile

While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N‐alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-05, Vol.2022 (18), p.n/a
Main Authors: Shrestha, Ganesh, Panza, Matteo, Singh, Yashapal, Stine, Keith J., Demchenko, Alexei V.
Format: Article
Language:English
Subjects:
Activation
Activation analysis
Alkylation
Carbohydrates
Glycosides
Glycosylation
Mechanism
NMR
Nuclear magnetic resonance
Oligosaccharides
Orthogonality
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Summary:While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N‐alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding of the mechanism led to a discovery of different activation pathways taking place with SIn versus SInR derivatives. Also investigated was orthogonality of the SInR leaving groups versus thioglycosides and selective activation of thioimidates over SInR glycosides. Protecting the nitrogen atom in the S‐indolyl leaving group of glycosyl donors helped to reduce the amount of NIS/TfOH required for their activation in glycosylation. The activation with silver salts shifted from the remote to the direct activation pathway offering additional insight into the reaction mechanism by which these leaving groups are activated.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200300