The synthesis of amino- and deutero- sugars from halo-cyclohexadiene-cis-diols

Abstract

A versatile method for the preparation of 2-amino-2-deoxy-, 3-amino-3-deoxy-, 4- amino-4-deoxy-, and 5-amino-5-deoxy-sugars from noncarbohydrate precursors, halobenzenes 1 (Figure 1), has been developed.

See: Figure 1: Aminosugar Targets from Halobenzenes

This methodology has also been applied to achieve the synthesis of protected D-mannose- 2,3,4,5,6-d₅ 191, and derivatives thereof, from the metabolite d₅- bromocyclohexadiene-cis-diol 189 obtained from the microbial oxidation of d₅- bromobenzene 2 (Figure 2).

See: Figure 2: Perdeuterated Sugar Synthesis