Chemical Glucosylation of Labile Natural Products Using a (2‐Nitrophenyl)acetyl‐Protected Glucosyl Acetimidate Donor
The synthesis of (2‐nitrophenyl)acetyl (NPAc)‐protected glucosyl donors is described that were designed for the neighboring‐group assisted glucosylation of base‐labile natural products also being sensitive to hydrogenolysis. Glycosylation conditions were optimized using a trichloroacetimidate glucosyl donor, and cyclohexylmethanol and (+)‐menthol as model acceptors. The approach was then extended to a one‐pot procedure for the synthesis of 1,2‐trans‐glycosides. This method was finally applied for improved synthesis of the masked mycotoxin T2‐O‐β,d‐glucoside.