A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using “Armed/Disarmed” Coupling and Selective Benzoylation and Sulfation

Abstract

In spite of the several attractive biological activities of the Lex, sLex, and sulfated Lex derivatives, there are still limitations in their practical syntheses. One of the most difficult problems is the many steps required for their syntheses. Therefore, we investigated simple constructions of the Lex analogs and succeeded in establishing highly practical syntheses of the Lex and sulfated Lex analogs. Especially, the “armed/disarmed” method allowed the first synthesis of Lex derivatives by a one-pot, two-step glycosylation. This synthetic strategy could be an applicable and useful method for oligosaccharide constructions of Lex, sulfated Lex, and other derivatives.