Synthetic Approaches Toward Ketopyranosides

January 30, 2024

• Title:       

  Synthetic approaches toward ketopyranosides

• Image Source:

  Carbene-mediated functionalization of the anomeric C-H bond of carbohydrates: Scope and limitations

• Figure Mark:

  Scheme 1

• Associated context:

  Following this approach, the new anomeric  carbon–carbon bond is readily obtained by addition of an  organometallic reagent to a d-lactone, yet the access to the  desired ketopyranosides is then strongly limited by the subsequent glycosylation step (Scheme 1a). Whereas a-anomers  were most often obtained in moderate yields,^[8,9] b-ketopyranosides exhibiting an equatorial aglycone were not accessible by this method, because 2-O-acyl protecting groups did  not provide the required anchimeric assistance.^[10]