摘要
以海藻中提取的海洋活性物质D-甘露醇为原料,先与丙酮发生缩合反应,将1,2,5,6位羟基保护起来,再对3,4位的羟基分别甲醚化、甲基磺酸和对甲苯磺酸酯化后,脱去异亚丙基保护基团,还原1,2,5,6位的羟基,对其进行硝酸酯化,合成了标题化合物,产率达到了77%以上。合成的中间体和目标产物的结构经红外光谱(IR)、核磁共振氢谱(1H-NMR)、碳谱(13C-NMR)和元素分析证实与其分子式相符。此外,还通过质谱(MS)分析对目标产物的分子量进行了分析,结果C35.76%,H3.22%,S9.45%,N8.30%与理论值C35.82%,H3.28%,S9.45%,N8.30完全相符。
D-mannitol, which was extracted from seaweeds, was used as crude materials, after being ac-etalated with acetone, hydroxyls of C-1,C-2,C-5 and C - 6 were protected. Then hydroxyls of C - 3 and C-4 were respectively etherealized with methyl iodide, sulfonated with mesyl chloride and tosyl chloride. After isopropylidenes were deprotected, hydroxyls of C-1,C-2,C-5 and C - 6 were nitrated under low temperature, and the title compounds were synthesized. The overall yield from D- mannitol with all the intermediates purified is from 33. 46% to 58. 66%. It is worth noting that the title compounds were easily afforded in a good yield of 78% - 83% through nitrating reaction. The structures of all intermediates and objective compounds were confirmed to be corresponded with their molecular formulas through IR,1H -NMR,13C -NMR and Element analysis. In addition, the molecular weight of title compounds was characterized by MS.
出处
《青岛大学学报（工程技术版）》
CAS
2005年第1期24-28,共5页
Journal of Qingdao University(Engineering & Technology Edition)
基金
中国科学院方向性创新项目(KZCX3-SW-215)国家杰出青年科学基金(4992514)
