Literature DB >> 28498382

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

Rashad R Karimov1, Derek S Tan, David 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.

Entities:  

Year:  2017        PMID： 28498382      PMCID： PMC5531170          DOI： 10.1039/c7cc01783a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


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