Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A: Via convergent B(C(6)F(5))(3)-catalyzed glycosylation of sterically-hindered precursors Journal Article


Authors: Karimov, R. R.; Tan, D. S.; Gin, D. Y.
Article Title: Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A: Via convergent B(C(6)F(5))(3)-catalyzed glycosylation of sterically-hindered precursors
Abstract: A convergent synthesis of the complex, doubly-branched pentasaccharide domain of the natural-product immunoadjuvant jujuboside A is described. The key step is a sterically-hindered glycosylation reaction between a branched trisaccharide trichloroacetimidate glycosyl donor and a disaccharide glycosyl acceptor. Conventional Lewis acids (TMSOTf, BF3·Et2O) were ineffective in this glycosylation, but B(C6F5)3 catalyzed the reaction successfully. Inherent complete diastereoselectivity for the undesired α-Anomer was overcome by rational optimization with a nitrile solvent system (1:5 t-BuCN/CF3Ph) to provide flexible, effective access to the β-linked pentasaccharide. © 2017 The Royal Society of Chemistry.
Journal Title: Chemical Communications
Volume: 53
Issue: 43
ISSN: 1359-7345
Publisher: Royal Society of Chemistry  
Date Published: 2017-05-01
Start Page: 5838
End Page: 5841
Language: English
DOI: 10.1039/c7cc01783a
PROVIDER: scopus
PMCID: PMC5531170
PUBMED: 28498382
DOI/URL:
Notes: Article -- Export Date: 2 August 2017 -- Source: Scopus
Altmetric Score
MSK Authors
  1. Derek S Tan
    68 Tan
  2. David Y Gin
    41 Gin