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Chem Commun (Camb). 2017 May 30;53(43):5838-5841. doi: 10.1039/c7cc01783a.

Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors.

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1
Tri-Institutional PhD Program in Chemical Biology, Memorial Sloan Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10065, USA. karimov.rashad@gmail.com.

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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