Abstract
AbstractA highly efficient and practical total synthesis of the sulfated ganglioside SM1a, a kind of human epithelial carcinoma antigen identified in mammalian kidney, has been accomplished for the first time. The characteristic sequence of SM1a, β‐D‐Galp‐(1→3)‐β‐D‐NHAcGalp‐(1→4)‐β‐D‐(3‐O‐sulfate)‐Galp‐(1→4)‐β‐D‐Glcp‐ceramide was assembled by a [3+2] convergent approach. A key trisaccharide building block was formed from a new galactose acceptor 7 containing a potential sulfated site, GalNHTroc donor 6, and galactose donor 4. The cyclic glucosyl ceramide was glycosylated with trisaccharide trichloroacetimidate 2 to give the protected ganglioside backbone in good yield. Selective sulfonation at the 3‐OH of the Gal residue followed by global deprotection gave the target molecule SM1a.
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