A direct conversion of aldohexopyranose to ketohexopyranose benzyl derivatives by Meerwein-Ponndorf/Oppenauer reaction induced by air-oxidised samarium diiodide

Article abstract of DOI:10.1016/0040-4039(96)01254-3

2,3,4,6-tetra-O-benzyl-D-galactopyranose and 2,3,4,6-tetra-O-benzyl-D-glucopyranose can be reduced at C-1 and oxidised at C-5 to give 1,3,4,5-tetra-O-benzyl-L-tagatopyranose and 1,3,4,5-tetra-O-benzyl-L-sorbopyranose, respectively, in good yields, through an intramolecular M-P/O reaction induced by preoxidised samarium diiodide.