S-Benzimidazolyl Glycosides as a Platform for Oligosaccharide Synthesis by an Active–Latent Strategy


  • This work was supported by awards from the NIGMS (GM077170), NIAID (AI067494), and AHA (0855743G). Lai-Ping (Pinky) Yan is thanked for the experimental assistance. Dr. Winter and Mr. Kramer (UM—St. Louis) are thanked for HRMS determinations.


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Doing the Biz: The S-benzimidazolyl (SBiz) anomeric moiety is a new leaving group that can be activated for glycosylation under a variety of conditions, including metal-assisted and alkylation pathways. Application of a substituted SBiz moiety (X=anisoyl, see picture) allows active–latent and armed–disarmed types of oligosaccharide assembly.