A Simple Synthesis of D-Galactono-1,4-Lactone and Key Building Blocks for the Preparation of Galactofuranosides
Résumé
The oxidation of D-galactose by Br-2 to yield D-galactono-1,4-lactone was developed and applied to the preparation of key building blocks for the synthesis of galactofuranosides. Three D-galactono-1,4-lactone derivatives protected as acetates, TBDMS ether, or acetonide were directly obtained in two steps on multigram scale with only one purification step. A mild deacetylation methodology afforded pure D-galactono-1,4-lactone and a new reduction of the lactone functionality using K-selectride was also optimized.