Synthesis of a teichoic acid fragment of Bacillus subtilis using a modified phosphotriester approach

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Abstract
The synthesis of a teichoic acid fragment (i.e. compound 8e), containing three 3‐O–(β‐glucopyranosyl)‐sn‐glycerol residues connected via two phosphodiester linkages, is described. The assemblage of the teichoic acid fragment was effected using a modified phosphotriester approach based on the use of 1‐hydroxybenzotriazole‐activated phosphorylating agents (i.e. phosphorylating agents 5c and 6c). Three suitably protected building blocks were prepared: i.e., 2b, 3c and 4b. Special attention was paid to the preparation of the middle unit 3c which contains a stable phosphodiester anilidate to avoid intramolecular reaction of the free hydroxyl function on phosphorus. Compound 2b was condensed with derivative 3c to give fragment 7a. The aniline group could be removed from dimer 7a to give 7b, which was then condensed with monomer 4b to give the fully protected teichoic acid fragment 8a. Stepwise removal of the protecting group of 8a afforded the teichoic acid fragment 8e.