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Visible Light Photoredox-Catalyzed O‑Sialylation Using Thiosialoside Donors

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journal contribution
posted on 06.06.2016, 00:00 by Yang Yu, De-Cai Xiong, Run-Ze Mao, Xin-Shan Ye
An efficient protocol for the O-sialylation using thiosialoside donors under visible light photocatalysis was developed. Thiosialosides were activated under the irradiation with blue light in the presence of Ru­(bpy)3(PF6)2 as photocatalyst, Umemoto’s reagent as CF3 radical source and Cu­(OTf)2 as an additive in acetonitrile/dichloromethane at −30 °C, and the subsequent reaction with glycosyl acceptors generally produced the desired sialosides in good to excellent yields with the satisfactory α-selectivity.