Total Synthesis of Carbohydrates: Stereoselective Syntheses of 2,6-Dideoxy-D-arabino-hexose and 2,6-Dideoxy-D-ribo-hexose

Article abstract of DOI:10.1021/jo00346a050

Short, highly stereoselective syntheses of the title carbohydrates from allylic alcohol precursors are described.A synthesis of the racemic arabino-deoxyhexose is also described.These syntheses feature the highly regioselective epoxide ring opening reactions of intermediates 7, 11, and 12 and the asymmetric epoxidation-kinetic resolution of allylic alcohol 10.