A catalytic Koenigs-Knorr glycosylation based on acceptor activation with In(NTf2)3

TETRAHEDRON

卷:74

Article

Li, Changwei¹  Liang, Haijing¹  Zhang, Zhan-xin¹  Wang, Zhaoyan¹  Yu, Lan¹  Liu, Huanxiang¹  An, Fengli¹  Wang, Shaohua¹  Ma, Lixia¹  Xue, Weihua¹ 

[1] Lanzhou Univ, Sch Pharm, Lanzhou 730000, Gansu, Peoples R China

关键词: Koenigs-Knorr glycosylation;    Acceptor activation;    In(NTf2)(3);    Catalytic;    Stereoselective;   

DOI  :  10.1016/j.tet.2018.05.080

来源: Elsevier

【 摘 要 】

The development of efficient glycosylation methods is important for gaining better insight into biological processes of significance to medicinal chemistry. Herein, we describe an In(NTf2)(3)-catalyzed Koenigs-Knorr glycosylation based on the activation of an alcoholic hydroxyl group. A catalytic amount of In(NTf2)(3) enables effective glycosylation of diverse alcohols with peracylated aldosyl bromides as donors, leading to the stereoselective formation of a series of glycosides in satisfactory yields. The protocol is characterized by mild reaction conditions and good functional-group tolerance, while obviating any need for any additive. Moreover, the potential utility of this transformation is demonstrated by the convenient syntheses of key building blocks for biomolecules of medicinal relevance. (C) 2018 Published by Elsevier Ltd.

【 授权许可】

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