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Lipophosphoglycans (LPGs) are found on the surface of Leishmania, a protozoan parasite, and are immunologically important. Herein, disaccharide 1‐phosphate repeating units of LPGs were successfully synthesized on a solid support with high anomeric purity using a disaccharide α‐1‐phosphoramidite building block. To enhance solubility in the reaction solvent, hydroxy‐protecting groups in the form of para‐t‐butylbenzoyl were introduced to the building block. The saccharide chain was elongated via stable glycosyl boranophosphate linkages, followed by the conversion of inter‐sugar linkages to phosphodiester counterparts using an oxaziridine derivative. The addition of a silylating reagent post‐reaction with the oxaziridine derivative efficiently facilitated the conversion of boranophosohodiesters to phosphodiesters. This method enabled the α‐selective synthesis of up to 15 repeating units, marking the longest homogeneous repeating units of LPGs synthesized chemically. Given the chain length equivalence to native LPGs, the method developed herein holds promise for advancing anti‐Leishmanial pharmaceuticals and vaccines. [ABSTRACT FROM AUTHOR]

This article, titled "Front Cover: α-Selective Solid-Phase Synthesis of Glycosyl Phosphate Repeating Structure Via the Phosphoramidite Method," discusses the synthesis of glycosyl phosphate repeating units found in lipophosphoglycans (LPGs) and capsular polysaccharides. The authors, K. Kawato, K. Sato, and T. Wada, describe their research on the α-selective solid-phase synthesis of these structures using glycosyl boranophosphates as stable intermediates. The cover art of the article depicts the structure of a synthesized disaccharide 1-phosphate repeating unit found in LPGs of Leishmania donovani. [Extracted from the article]