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:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021745847&doi=10.1039%2fc7cc01783a&partnerID=40&md5=51c07a23ec1aae4c4916ce0ed083e662
Notes:	Article -- Export Date: 2 August 2017 -- Source: Scopus

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