Developing efficient and stereoselective glycosylation reactions remains one of the more challenging endeavors in organic synthesis. This holds especially true in cases such as β-linked deoxy-sugars, where the outcome of the glycosylation cannot be controlled using the stereochemical information intrinsic to the glycosyl donor. In order to address this issue, our group has been exploring approaches to glycosylation where the stereochemical outcome of the reaction is controlled entirely by the promoter. Previously, we had found that p-toluenesulfonic anhydride activates deoxy-sugar hemiacetals as α-glycosyl tosylates, which react stereoselectively with nucleophilic acceptors to produce β-linked products. In order to improve the utility and generality of the reaction, we assessed if the more robust p-toluenesulfonyl chloride could be used as an alternative promoter. We have found that the use of this sulfonyl chloride greatly simplifies the procedure and permits gram-scale glycosylation reactions without eroding selectivity. The development of this third generation approach and its application to the construction of β-linked deoxy-sugar oligosaccharides will be presented.

Improved approach to the direct construction of 2-deoxy-β-linked sugars: Applications toward oligosaccharide synthesis

256th National Meeting (2018)

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