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

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 method...

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Bibliographic Details
Published in:Carbohydrate research 2022-08, Vol.518, p.108579-108579, Article 108579
Main Authors: Takahashi, Daisuke, Inaba, Kazuki, Toshima, Kazunobu
Format: Article
Language:English
Subjects:
1,2-cis glycoside
Boron-mediated aglycon delivery
Glycosylation
Natural products
Regioselective
Stereoselective
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Summary: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. [Display omitted] •Regio- and β-stereoselective rhamnosylation and its application are described.•Regio- and 1,2-cis-stereoselective glycosylation of unprotected glycosides and its application are described.•Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols and its application are described.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2022.108579