A unified strategy for the synthesis of aldohexoses by boronate assisted assembly of CH2X2 derived C-1-building blocks

A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C-1-units is reported. The underlying synthesis of C-6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realized for every glycol motif by strategic variation of the sequence.

Automated summary

This article presents a synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C-1-units. The synthesis of C-6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been achieved for every glycol motif by strategic variation of the sequence.