Synthesis And Research Of Six-membered Azasugars From D-Mannitol

In this thesis, the recent methods of synthesizing azasugars and the modification were firstly reviewed, By using D-mannitol as the starting materials for the synthesis of azasugar, a series of azasugar compounds were stereoselectively synthesized. The main result obtained are as follows:1.Using D-mannitol as the starting materials, the gloceraldehyde compound 1 was synthesized through multi-step reaction. then compound 2 was synthesized via Henry reaction. after hydrolysis and selective tosylation of primary hydroxyl group afforded compound 3, we obtained compound 4 with the two free hydroxyl groups were protected by acetone, finally six-membered azasugars 5 and 6 were synthesized by Mannich reaction between the compound 4 and amino.2.The compound 7 was got from Compound 3 after elimination and Herry reaction, after hydrolysis and selective tosylation of primary hydroxyl group afforded compound 8 and 9.3.Using D-glucose as the starting materials, carbonyl compound 10 was synthesized in the presence of acetylacetone, after selective tosylation of primary hydroxyl group afforded compound 11. on the condition of alkaline, the reaction between compound 11 and hydroxylamin hydrochloride generated oxime compound 12.In the thesis, we have obtained 15 compound, including 7 new compounds. the structures of this new compounds were confirmed by MS、1H NMR、13C NMR、IR spectra.