Chemical Diversification of Sialic Acid Glycosides by Stereospecific, Chemoselective Deamination


  • We thank the NIH (GM 62160) for support of this work, and Dr. P. K. Kancharla for experimental assistance.


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Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late-stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort.