Direct chemical glycosylation with pentenyl- and thioglycoside donors of N-acetylglucosamine

作者：Krag Jonas; Christiansen Mira S; Petersen Jette G; Jensen Henrik H^*

来源：Carbohydrate Research, 2010, 345(7): 872-879.

DOI：10.1016/j.carres.2010.02.013

• NIS activation
• Metal triflate
• Transient oxazoline intermediate

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.

• 出版日期2010-5-7