Template-directed synthesis is a broadly employed strategy by Mother Nature in the assembly of biomolecules in a living system. In this presentation, we report our effort to design a practical redox cascade system to enable the template-directed stereoselective generation of 1,2-cis glycosidic linkage in the chemical synthesis of complex oligosaccharides. This work stems from our early works on the development of 1) a sequential redox process to enable a one-pot single step intramolecular aglycan delivery reaction for the selective preparations of �-mannosides and �-rhamnosides;1 2) and a photoredox process for programmable catalytic glycosylations with seleno-/thio-glycosides.2 Discussions will be focused on the practical applicability of the newly developed system and the preparation of oligosaccharides containing continuous 1,2-cis glycosidic linkages in both solution and solid phases in the context of their roles in modulating innate immune response. 1. Liu, X.  Abstracts of Papers, 245th ACS National Meeting & Exposition, New Orleans, LA, United States, April 7-11, 2013, ORGN-514. 2. Liu, X.  Abstracts of Papers, 243rd ACS National Meeting & Exposition, San Diego, CA, United States, March 25-29, 2012, CARB-5.

Towards a practical redox cascade system for template-directed stereoselective glycosylation

247th National Meeting (2014)

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