Synthesis And Research Of Novel Azasugars From D-Mannitol

In this thesis, based on the investigation of the kinds of azasugars, the synthetic methods of the azasugars, such as the bringing of nitrogen, the formation methods of cyclic compounds, new method was established to synthesize the azasugars from D-mannitol by Herry reaction, Wittig reaction and Mannich reaction and so on. The main results obtained are-as follows:1. Using D-mannitol as the material,1,2-5,6-Diisopropylidene-D-mannitol compound2was synthesized in the presence of the anhydrous zinc chloride in the dry acetone. Then the2,3-O-Isopropylidene-D-glyceraldehyde was prepared in excellent yield. Herry reaction of compound3with Nitromethane provided Nitro-compound4. After Acid hydrolysis opening of the ketal got compound5. Selective tosylation of compound5afforded compound6. At last three azasugars, compound7, compound8and compound9, were obtained via Mannich reaction of the compound6and amino and formaldehyde. Synthesis route as follows:2. Compound10was got from compound6by TsOH as catalyst and acetone as solvent. Synthesis route as follows: 3. Using D-mannitol as the material,1,2-5,6-Diisopropylidene-D-mannitol was obtained via propylidene protection.2,3-O-Isopropylidene-D-glyceraldehyde was obtained by oxidative cleavage of the diol, followed by Wittig reaction of the resulting aldehyde afforded the unsaturated ester13. Synthesis route as follows:In the thesis, we have obtained10compounds containing6new compounds, and these compounds have been characterized by IR, MS,13C NMR and1H NMR.Preliminary studies of the synthesis of azasuagrs have been done.