Crude<i>D</i>‐(+)‐Glyceraldehyde Obtained from<i>D</i>‐Mannitol‐Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species

Abstract

Abstract The oxidative cleavage of D‐(+)‐mannitol‐diacetonide with sodium periodate lead to a mixture of D‐(+)‐glyceraldehyde, its hydrate and oligomeric derivatives. In spite of the low concentration of free glyceraldehyde (estimated in ∼20%, by NMR), good yields were obtained in nucleophilic additions involving this mixture and a variety of nucleophiles (amines, phosphonates, phosphoranes, nitronates, organometallic compounds).