Synthesis of the Antigenic Tetrasaccharide Side Chain from the Major Glycoprotein of Bacillus anthracis Exosporium

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Abstract
A synthesis of the pentenyl glycoside of the tetrasaccharide side chain from the major glycoprotein of Bacillus anthracis by a [3 + 1] approach is described. The construction of the 1,2-trans-glycosidic linkage in the terminal anthrose moiety was achieved through the application of known α-nitrilium ion-mediated β-selective glycosylation methodology. An iterative glycosylation strategy was used for the assembly of the trirhamnan building block. A new route to the anthrose saccharide was developed from d-galactose.