Light fluorous synthesis of glucosylated glycerol teichoic acids

[Display omitted] ► Two fluorous linker systems have been developed for the assembly of teichoic acids. ► Glucosylated TAs with a terminal phosphate or hydroxyl group can be synthesized. ► Light fluorous synthesis is a powerful means to rapidly assemble teichoic acids. [Display omitted] We here describe the synthesis of glucosylated teichoic acid (TA) fragments using two complementary fluorous scaffolds. The use of a perfluorooctylpropylsulfonylethyl (F-Pse) linker in combination with (glucosyl)glycerol phosphoramidite building blocks allows for the assembly of TA fragments with a terminal phosphate mono-ester, whereas the use of a perfluorooctylsuccinyl spacer delivers TA oligomers featuring a terminal alcohol functionality. These complementary linker systems have been developed because the nature of the TA chain terminus can play a role in the biological activity of the synthetic TAs. A novel α-glucosylated glycerolphosphoramidite building block is introduced to allow for a robust light fluorous synthetic protocol.