Literature DB >> 35598560

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

Daisuke Takahashi1, Kazuki Inaba2, Kazunobu Toshima2.   

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.
Copyright © 2022 Elsevier Ltd. All rights reserved.

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Keywords:  1,2-cis glycoside; Boron-mediated aglycon delivery; Glycosylation; Natural products; Regioselective; Stereoselective

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Year:  2022        PMID: 35598560     DOI: 10.1016/j.carres.2022.108579

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  1 in total

Review 1.  Recent advances in stereoselective 1,2-cis-O-glycosylations.

Authors:  Akihiro Ishiwata; Katsunori Tanaka; Jiaming Ao; Feiqing Ding; Yukishige Ito
Journal:  Front Chem       Date:  2022-08-19       Impact factor: 5.545

  1 in total

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