Boron-mediated aglycon delivery (BMAD) for the stereoselective synthesis of 1,2-cis glycosides

Research output: Chapter in Book/Report/Conference proceedingChapter


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.

Original languageEnglish
Title of host publicationSpecial Volume in Memory of Hidetoshi Yamada Part 2
EditorsDavid C. Baker
PublisherAcademic Press Inc.
Number of pages27
ISBN (Print)9780323985970
Publication statusPublished - 2022 Jan

Publication series

NameAdvances in Carbohydrate Chemistry and Biochemistry
ISSN (Print)0065-2318


  • 1,2-cis Glycosides
  • BMAD
  • Boron-mediated aglycon delivery
  • Glycolipids
  • Glycosylation
  • Natural glycosides
  • Regioselective
  • Stereoselective
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry


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