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  • Title: Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine.
    Author: Krag J, Christiansen MS, Petersen JG, Jensen HH.
    Journal: Carbohydr Res; 2010 May 07; 345(7):872-9. PubMed ID: 20304386.
    Abstract:
    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.
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