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硼介导的糖苷配基传递(BMAD)在高效合成 1,2-顺式糖苷中的最新进展。

Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides.

机构信息

Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.

Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.

出版信息

Carbohydr Res. 2022 Aug;518:108579. doi: 10.1016/j.carres.2022.108579. Epub 2022 May 13.

Abstract

Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

摘要

高立体选择性合成 1,2-顺式糖苷仍然是一项具有挑战性的任务,因为糖基供体中的 2-O-酰基功能缺乏可靠的邻基参与(NGP)。在这种情况下,我们小组最近开发了使用有机硼试剂和 1,2-脱水糖基供体的高度 1,2-顺式立体选择性糖苷化方法,命名为硼介导的苷元传递(BMAD)。在这篇迷你综述文章中,我们介绍了 BMAD 方法及其在合成生物活性天然产物和复杂糖苷中的应用,这些内容自我们 2017 年在该期刊上发表这篇迷你综述文章以来已有报道。

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