2-Allylphenyl glycosides as glycosyl donors for sugar coupling

Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins.

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► 2-Allylphenyl glycoside is herein introduced as a new type of stable glycosyl donor.
► The optimum promoter identified for this donor is the ICl/AgOTf combination.
► Alpha-mannosylations of sugar acceptors and other alcohols were demonstrated.
► The protocol was also applied in the assembly of the bleomycin sugar fragment.