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Direct sialic acid 4-OAc substitution by nitrogen, sulfur and carbon nucleophiles with retention of stereochemistry.

Tiago BozzolaUlf J NilssonUlf Ellervik
Published in: RSC advances (2022)
A direct one-step nucleophilic substitution of the 4-OAc of acetyl protected Neu5Ac is presented. Previously published methods for direct substitution of the 4-OAc are limited to cyclic secondary amines. Here we present conditions that allow for a much wider range of nitrogen nucleophiles as well as thiols and cyanide, to be used. The present investigation significantly broadens the scope of 4-aminations and allows for the introduction of a wide variety of different nucleophiles.
Keyphrases
  • randomized controlled trial
  • fluorescent probe
  • meta analyses