Bromodimethylsulfonium bromide/silver triflate-promoted glycosylations using glycosyl allenoates as donors

• Glycosyl 3,3-dimethyl-4,5-allenoates as donors are easily prepared.
• Oligosaccharides are obtained by treating glycosyl allenoates with alcohols.
• The glycosylations proceed smoothly under the promotion of BDMS/AgOTf.
• Allenic group is critical for the glycosylation of glycosyl allenoate.

A series of novel glycosyl allenoates were prepared by condensions of hemiacetals with 3,3-dimethyl-4,5-allenoic acid. Their glycosylations with various alcohols under the promotion of bromodimethylsulfonium bromide/silver triflate smoothly proceeded to produce disaccharides. Studies reveal that allenic group is crucial for the efficient glylcosylation of glycosyl allenoate.

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