Synthesis of 12-O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Fifteen glycosyl-oxystearates were synthesized by Crich’s 4,6-benzylidene and Koening–Knorr strategies. Assessment of structure–activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated T cells (NFAT)-green fluorescent protein (GFP) revealed that four dimannopyranosyl-oxystearate analogues were Mincle agonists and that 12-O-(2-O-α-d-mannopyranosyl)-α-d-mannopyranosyl-oxystearate was as an activator of both mouse and human Mincle.