De novo synthesis of a D-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from Sphingomonas yanoikuyae.
A concise synthesis of a differentially protected D-galacturonic acid (D-GalA) thioglycoside and the construction of a potent immunomodulating glycosphingolipid are described. The key steps of the synthesis are an Evans aldol reaction between a C4 aldehyde and a PMB-protected glycolyloxazolidinone as well as a tandem-PMB-deprotection/cyclization to thioglycosides. The key glycosylation step is optimized by varying the anomeric leaving group, the activating agent, and the solvent system.
Stallforth
Pierre
P
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zurich, Wolfgang-Pauli-Strasse 10, Zurich, Switzerland.
Adibekian
Alexander
A
Seeberger
Peter H
PH
D006028:Glycosphingolipids / Q000138:chemical synthesis*; D020578:Sphingomonas / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis*
D006028:Glycosphingolipids; D013865:Thioglycosides