Bimodal Glycosyl Donors Protected by 2-O-(ortho-Tosylamido)benzyl Group
2018
Ding, Feiqing | Ishiwata, Akihiro | Ito, Yukishige
A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf₂NH. On the other hand, activation by TfOH in Et₂O provided α-glycosides as major products. This “single donor” approach was employed to assemble naturally occurring trisaccharide α-d-Glc-(1→2)-α-d-Glc-(1→6)-d-Glc and its anomers.
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