Preparation of 6,6,1′,1′,6′,6′-hexadeutero sucrose

The preparation of 6,6,1′,1′,6′,6′-hexadeutero sucrose is reported. The synthesis is based on a triple oxidation of a protected sucrose 6,1′,6′-triol to the corresponding 6,1′,6′-tricarboxylic acid or ester, followed by reduction with lithium aluminium deuteride. This triple oxidation could be achieved either using cat. TEMPO–NaOCl (to the acid) or PDC–Ac2O–t-BuOH (to the t-butyl carboxylic ester).