Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6 F5 )3 -catalyzed glycosylation of sterically-hindered precursors

Chemical Communications : Chem Comm
Rashad R KarimovD Y Gin

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.

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Citations

Mar 25, 2020·Journal of the American Chemical Society·Girish C SatiJohn Montgomery
Jul 4, 2018·Chemical Reviews·Michael Martin Nielsen, Christian Marcus Pedersen
Mar 15, 2018·The Journal of Organic Chemistry·Kunj Bihari MishraJeyakumar Kandasamy
Sep 12, 2020·Chemical Reviews·Wen-Hao Li, Yan-Mei Li

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