烷基-β-D-吡喃木糖苷的合成及性能  

Synthesis and properties of alkyl β-D-xylopyranosides

作　　者：旷娜[1] 伍桂龙[1] 陈朗秋[1] 夏殊[1] 李贞操 陈国勇[1] 叶雪[1] KUANG Na WU Guilong CHEN Langqiu XIA Shu LI Zhencao CHEN Guoyong YE Xue(Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China)

机构地区：[1]湘潭大学化学学院,环境友好化学与应用省部共建教育部重点实验室,湖南湘潭411105

出　　处：《中南大学学报（自然科学版）》2016年第10期3323-3331,共9页Journal of Central South University:Science and Technology

基　　金：湖南省自然科学基金资助项目(14JJ2067,10JJ6023);湘潭大学第十批大学生创新基金资助项目(2014xtuxj31)~~

摘　　要：采用三氯乙酰亚胺酯法,以D-木糖为原料,经全乙酰化、C1位选择性脱乙酰基,转化成三氯乙酰亚胺酯,以一系列醇为受体与之进行偶联反应及脱保护,选择性地合成9种不同碳链长度的烷基-β-D-吡喃木糖苷。目标化合物经核磁共振技术对结构进行表征,利用偏光显微镜、热分析仪等对其性能进行测试。研究结果表明:正辛基和正壬基-β-D-吡喃木糖苷在低浓度时能使表面张力下降到较低值,且具有较好的发泡性,正壬基-β-D-吡喃木糖苷有较好的乳化性;当烷基链长n≤9时,烷基-β-D-吡喃木糖苷的溶解熵都随温度升高呈下降趋势;当n为7和8时,其糖苷具有较大的溶解焓;目标化合物均具有液晶现象。Using the trichloroacetimidate method and taking D-xylose as a raw material, nine kinds of carbon chain length alkyl β-D-xylopyranosides were synthesized selectively through acetylation, selective deacetylation at C1 position, and conversion to trichloroacetimidate, coupling with a series of acceptors alcohols and deprotection. The structures of target compounds were characterized by NMR technology, and their properties were tested by polarization microscopy（POM）, thermal gravimetric analysis（TGA）, etc. The results show that the n-octyl and n-nonyl β-D-xylopyranosides are able to make surface tension decrease to a low value and possess better foaming properties, while n-nonyl β-D-xylopyranoside has better emulsification. However, with the increase of temperature, dissolution entropies of all alkyl β-D-xylopyranosides decrease when the chain length of alkyl group is less than 9. The dissolution enthalpies of D-xylopyranosides are bigger when the chain length of alkyl groups are 7 and 8. All alkyl β-D-xylopyranosides can form thermotropic liquid.

关 键 词：木糖 烷基-β-D-吡喃木糖苷 发泡 乳化 表面张力 

分 类 号：O629.113[理学—有机化学]