Fluorinated 1,5-dideoxy-1,5-iminoalditols: synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol (1,6-dideoxy-6-fluoronojirimycin) and 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol)

Abstract

An efficient synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol 13 from inexpensive L-sorbose by way of reductive amination of 12 is described. Synthesis of 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol)19 has been achieved also by a route which involves fluorination of 16 with retention of configuration at C-4.