Journal
CARBOHYDRATE RESEARCH
Volume 345, Issue 7, Pages 872-879Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.02.013
Keywords
NIS activation; Metal triflate; Transient oxazoline intermediate
Funding
- Danish National Science Research Foundation
- Carlsberg Scholarship
- OChem Graduate School, Aarhus University
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The use of pentenyl and thiophenyl glycosides of N-acetylglucosamine (GlcNAc) as glycosyl donors for the direct preparation of O-glycosides of GlcNAc promoted by N-iodosuccinimide (NIS) and metal triflates in dichloromethane has been investigated. Both glycosyl acceptors 1-octanol and (-)-menthol resulted in good glycosylation yields for both types of donors with pentenyl glycosides being somewhat superior in terms of yield. Carbohydrate-based acceptors were reacted with a benzylated GlcNAc-pentenyl donor but only provided disaccharides in poor to moderate yields. The results show that a variety of metal triflates are capable of acting as an activator for both NIS and the intermediate oxazoline. (C) 2010 Elsevier Ltd. All rights reserved.
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