Synthesis of 2-acetylnoviosamine derivatives by hydrogenolytic cleavage of a spirocyclopropane

Abstract

The preparation of a 2-acetamido derivative of the rare 5,5-gem-dimethyl-deoxy carbohydrate noviose is reported in this study. The synthesis starts from readily available N-acetyl-D-mannosamine and tackles the introduction of the gem-dimethyl structural feature via a cyclopropanation and hydrogenolytic cleavage strategy, which can enable the synthesis of 2-amino noviose derivatives of both L- and D-noviose.