Synthesis of β-(1→2)-Linked 6-Deoxy-<scp>l</scp>-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an <i>ortho</i>-Hexynylbenzoate Donor

Abstract

The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica O:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-l-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh₃AuNTf₂. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation.