Abstract
We have succeeded in developing a novel glycosidation catalyzed by a combination of trimethylsilyl bromide (TMSBr) and a Lewis acid using simple O-glycosides as glycosyl donors. Treatment of benzyl 2-deozy-2-tri-chloroethoxycarbonylamino-D-glucopyranoside with TMSBr and zinc bromide in the presence of glycosyl acceptors gave α-O-glycosides in moderate to high yields. Zinc triflate and tin(II)triflate were also found to be effective as the Lewis acid. This new methodology is applicable to methyl D-glucopyranoside.
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