Research On Synthesis And Application Of 2,3,6-trideoxy-2-fluoro-3-aminohexose

3-amino-2,6-dioxysaccharides are important components of many antineoplastic antibiotics and antibiotics.Meanwhile,fluorination is a common technique for the modification of drug molecules in commemoratory medicinal chemistry.This dissertation describes the synthesis and application of 2-fluoro-3-amino-2,6-dioxysaccharides,which can be divided in the following three parts:1.We have developed an efficient method for the synthesis of 2,3,6-trideoxy-2-fluoro-3-aminohexose using electrophilic fluorination of glycals bearing different masked nitrogen groups as the key step.A series of 2-fluoro-L-Ristosamine and its lactone derivatives were synthesized.2.We have developed an efficient route for the synthesis of(R)-2-L-Ristosamine derivatives using organocatalytic ?-fluorination of ?-aminoaldehyde as the key step.This route is suitable for the synthesis of its enantiomer,(S)-2-fluoro-D-Ristosamine.3.We have synthesized different glycosyl donors derived from 2-fluoro-3-amino-2 and attempted the ensuring glycosylation.All the work conducted in this thesis would provide useful information and data for further research on 3-amino-2,6-dioxysaccharide in our group.