Synthesis of hexaarabinofuranoside bearing the 4-(3-azidopropoxy)phenyl aglycone related to the terminal fragment of polysaccharides of mycobacteria.

A convergent synthesis α-(1→3)-, α-(1→5), β-(1→2)-linked hexaarabinofuranoside related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria as a glycoside with 4-(3-azidopropoxy)phenyl aglycone was accomplished. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can be used as both a temporary protective group for the anomeric position of the carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates. The key step of the synthesis is the formation of 1,2-trans glycosidic linkage with the use of Ara-β-(1→2)-Ara p-tolylthioarabinofuranoside bearing five triisopropylsilyl groups. [ABSTRACT FROM AUTHOR]