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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]

A convergent synthesis of tetraarabinofuranoside β-d-Araf-(1→2)-α-d-Araf-(1→3)-α-d-Araf-(1→5)-α-d-Araf-1↑OR (R is 4-(3-azidopropoxy)phenyl) related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria was developed. The synthesized tetraarabinofuranoside represents a linear motif of a branched hexaarabinofuranoside, which is the main LAM epitope. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can serve as both a temporary protective group for the anomeric position of carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates useful for the development of new tuberculosis diagnostic assays. The key step of the synthesis is the formation of 1,2-cis-glycosidic bond. [ABSTRACT FROM AUTHOR]

A convergent synthesis of arabinofuranose-based, α-(1→5), β-(1→2)-linked tetrasaccharide related to the terminal fragment of lipoarabinomannan and arabinogalactan of mycobacteria was carried out. The tetrasaccharide was synthesized as a glycoside with 4-(2-azidoethoxy)phenyl aglycone belonging to the class of Janus aglycones, which can serve as both a temporary protective group of the anomeric position of the carbohydrate residue and a (pre)spacer for the synthesis of neoglycoconjugates (NGCs) useful in the development of new diagnostic agents for tuberculosis. The key step is the formation of a 1,2-cis-glycosidic bond. [ABSTRACT FROM AUTHOR]