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Design and Synthesis of Novel Isosorbide Nitrate Analogues from 1, 4:3, 6-dianhydro-D-Fructose

Author: SongXiaoPing
Tutor: LiuHongMin;LiuFengWu
School: Zhengzhou University
Course: Medicinal Chemistry
Keywords: 1，4，6-dianhydro-D-fructose C12 higher carbon sugar nitration nitrate ester
CLC: R914
Type: Master's thesis
Year: 2007
Downloads: 48
Quote: 0
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Abstract


In this thesis, through nitration with hybrid acid, two mother compounds 1R-（isomannid-2-yl）-1,4:3,6-dianhydro-D-fructose 5,5’-dinitrate and 1,4:3,6-dianhydro-D -fructose 5 -nitrate were synthesized using 1,4:3,6-dianhydro-D-fructose and C12 higher carbon sugar derived from 1,4:3,6-dianhydro-D-fructose as the starting materials, and the optimization of the reaction condition was discussed correspondingly. In the study on the Henry Reaction, an interesting kinetic and thermodynamic controlled reaction phenomenon was found. All the reaction products were elucidated by single-crystal X-ray crystallographic analysis. Through the single-crystal X-ray crystallographic analysis we found that the configuration at C-1 of 1R-（isomannid-2-yl）-1,4:3,6-dianhydro-D-fructose 5, 5’-dinitrate had changed in the Henry reaction with nitroethane. The corresponding reaction mechanism was studied. A series of other nitrate derivatives were synthesized, which are of great value in biological activity evaluation and structure-activity analysis.1. Synthesized the l,4:3,6-dianhydro-D-fructose 5 -nitrate by using a solution of nitric acid （ 98%） and sulfuric acid （98%）. In the optimization of the reaction conditions we found the best condition of this reaction is 3 equiv nitric acid（98%）, nH2SO4/nHNO3 is 3:1 and the time is 3 hours.Through Henry Reaction two nitrate ester derivatives were synthesized and the stereochemistry of the reaction was discussed. 2. Synthesized the 1R-（isomannid-2-yl）-1,4:3,6-dianhydro-D-fructose 5, 5’-dinitrate in high yield by using a solution of nitric acid （98%） and sulfuric acid （98%）.3. In the Henry Reaction we found an interesting kinetic and thermodynamic controlled phenomenon. The kinetic and thermodynamic controlled reactions with nitromethane were carried out to afford （S-） and （R-）β-nitroalcohols respectively. But with nitroethane the reaction gave a （S-）β-nitroalcohol with a changed configuration at vicinal carbon, in which two stereogenic centers were generated and one altered. The configuration of these compounds all were elucidated by single-crystal X-ray crystallographic analysis. 4. A series of other nitrate ester compounds were synthesized by using the 5, 5’-dinitrate C12 higher carbon sugar as the starting material, which are of great value in biological activity evaluation and structure-activity analysis. In the thesis, 18 compounds including 17 new compounds were synthesized. All the compounds were characterized by HRMS, 1H NMR, 13C NMR, IR spectra. The absolute configurations for 6 new compounds among them were confirmed by X-ray crystallographic analysis. The bioactivity investigation was in processing.

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