{"title":"Boron-mediated aglycon delivery (BMAD) for the stereoselective synthesis of 1,2-cis glycosides.","authors":"Daisuke Takahashi, Kazunobu Toshima","doi":"10.1016/bs.accb.2022.10.003","DOIUrl":null,"url":null,"abstract":"<p><p>1,2-cis Glycosides are frequently found in biologically active natural products, pharmaceutical compounds, and highly functional materials. Therefore, elucidating the role of mechanism of their biological activities will help clarify the structure-activity relationships of these diverse compounds and create new lead compounds for pharmaceuticals by modifying their structures. However, unlike 1,2-trans glycosides, the stereoselective synthesis of 1,2-cis glycosides remains difficult due to the nonavailability of neighboring group participation from the 2-O-acyl functionalities of the glycosyl donors. In this context, we recently developed organoboron-catalyzed 1,2-cis-stereoselecitve glycosylations, called boron-mediated aglycon delivery (BMAD) methods. In this review article, we introduce the BMAD methods and several examples of their application to the synthesis of biologically active glycosides.</p>","PeriodicalId":7215,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"82 ","pages":"79-105"},"PeriodicalIF":0.0000,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advances in carbohydrate chemistry and biochemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1016/bs.accb.2022.10.003","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 0
Abstract
1,2-cis Glycosides are frequently found in biologically active natural products, pharmaceutical compounds, and highly functional materials. Therefore, elucidating the role of mechanism of their biological activities will help clarify the structure-activity relationships of these diverse compounds and create new lead compounds for pharmaceuticals by modifying their structures. However, unlike 1,2-trans glycosides, the stereoselective synthesis of 1,2-cis glycosides remains difficult due to the nonavailability of neighboring group participation from the 2-O-acyl functionalities of the glycosyl donors. In this context, we recently developed organoboron-catalyzed 1,2-cis-stereoselecitve glycosylations, called boron-mediated aglycon delivery (BMAD) methods. In this review article, we introduce the BMAD methods and several examples of their application to the synthesis of biologically active glycosides.
1,2-顺式糖苷经常存在于具有生物活性的天然产物、药物化合物和高功能材料中。因此，阐明其生物活性的作用机制将有助于厘清这些不同化合物的构效关系，并通过修饰其结构来创造新的药物先导化合物。然而，与1,2-反式糖苷不同，1,2-顺式糖苷的立体选择性合成仍然很困难，因为糖基供体的2- o -酰基官能团无法参与邻基的合成。在这种背景下，我们最近开发了有机硼催化的1,2-顺式立体选择性糖基化，称为硼介导的糖基传递(BMAD)方法。本文综述了BMAD方法及其在生物活性苷类化合物合成中的应用。
期刊介绍：
Advances in Carbohydrate Chemistry and Biochemistry has provided, since its inception in 1945, critical and informative articles written by research specialists that integrate the industrial, analytical, and technological aspects of biochemistry, organic chemistry, and instrumentation methodology to the study of carbohydrates. Its articles present a definitive interpretation of the current status and future trends in carbohydrate chemistry and biochemistry.
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