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Significance Despite their dominant role as electrophiles in biosynthetic pathways promoted by enzymes, organic phosphates are rarely employed in laboratory synthesis, because phosphates are generally very poor leaving groups. Here we report that a bis-thiourea catalyst promotes β-selective glycosylation reactions of phosphate donors under mild, neutral conditions. The catalytic method enables glycosylation of peptides, complex natural products, and pharmaceutical agents bearing a variety of reactive functionalities, thereby representing an important step toward enabling convenient access to glycosylated chemical matter of interest to synthetic chemists and chemical biologists.

Catalytic activation of glycosyl phosphates for stereoselective coupling reactions