【摘要】：本篇論文首先對核苷類藥物以及核苷類化合物的結(jié)構(gòu)修飾進(jìn)行了綜述，然后以D-葡萄糖為原料進(jìn)行了擬螺核苷的合成研究，利用Wittig反應(yīng)、Michael加成反應(yīng)、Mannich反應(yīng)和Henry反應(yīng)等，立體選擇性的合成一系列的葡萄糖擬螺核苷類似物，本文所取得進(jìn)展情況如下： 一、以D-葡萄糖為原料，經(jīng)過兩步反應(yīng)得到氧化糖1，然后通過Wittig反應(yīng)，Michael加成反應(yīng)得到化合物3，最后通過對化合物3的Mannich反應(yīng)得到葡萄糖擬螺核苷化合物4，5，6，7，8，9，10。其中6和7，8和9分別是立體異構(gòu)體。 (a)干燥的CH3COCH3,濃H2SO4;(b) PDC, DCM, Ac2O;(c) Wittig試劑, CHCl3;(d) CH3NO2,DBU;(e) HCHO, C2H5OH, R-NH2 二、以D-葡萄糖為原料，經(jīng)過四步反應(yīng)得到飽和硝基化合物11，之后通過上Ts保護(hù)其中的6位羥基。(a)干燥的CH3COCH3,濃H2SO4;(b) PDC, DCM, Ac2O;(c) CH3NO2, THF, KF;(d) CH3OH,H2O,冰乙酸;(e) TsCl, Py 三、以D-葡萄糖為原料，，經(jīng)多步反應(yīng)得到不飽和硝基化合物13，然后通過Michael加成反應(yīng)得到化合物14，最后通過羥基脫保護(hù)、上Ts得到化合物16。 (a) DMSO, Ac2O;(b) CH3NO2,無水THF, NaH;(c) CH3OH, H2O,冰乙酸;(d) TsCl, Py 在本論文中，共合成了18種化合物，其中13個化合物是新化合物，通過1H NMR，13C NMR，HR-MS，IR等分析方法對新化合物進(jìn)行了結(jié)構(gòu)表征。
[Abstract]:In this paper, the structure modification of nucleoside drugs and nucleoside compounds was reviewed, and then the synthesis of spiroside from D- glucose was studied. Wittig reaction, Michael addition reaction, Mannich reaction and Henry reaction were used. The progress of stereoselective synthesis of a series of glucospironoside analogues is as follows: first, using D-glucose as raw material, After two steps of reaction, sugar oxide 1 was obtained, then compound 3 was obtained by Wittig reaction and Michael addition reaction. Finally, the glucospironoside compound 4H5, 6, 7, 7, 8, 10 was obtained by the Mannich reaction of compound 3. Of these, 6 and 7, 8 and 9 were CH3COCH3, concentrated H _ 2SO _ 4 dried by stereoisomer. (a), respectively, and (b) PDC, DCM, Ac2O; (c) Wittig reagent, CHCl3; (d) CH3NO2,DBU; (e) HCHO, C _ 2H _ 5OH, R-NH2 _ 2, were used as raw materials for D- glucose. After four steps of reaction, saturated nitrocompound 11 was obtained, and then the 6 hydroxyl. (a) dried CH3COCH3, concentrated H _ 2SO _ 4 was protected by Ts, and (b) PDC, DCM, Ac2O; (c) CH3NO2, THF, KF; (d) CH3OH,H2O, acetic acid; (e) TsCl, Py _ 3 was used as raw material for D- glucose. The unsaturated nitro compound 13 was obtained by multistep reaction, then compound 14 was obtained by Michael addition reaction. Finally, the compound was protected by hydroxyl deprotection. (a) DMSO, Ac2O; (b) CH3NO2, anhydrous THF, NaH; (c) CH3OH, H 2O and acetic acid; (d) TsCl, Py in this thesis, 18 compounds were synthesized, 13 of which were new compounds. The structure of the new compound was characterized by 1H NMR,13C NMR,HR-MS,IR et al.
【學(xué)位授予單位】：鄭州大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914.5

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