烷基-β-D-吡喃葡萄糖苷的合成与性能

doi:10.3724/SP.J.1095.2013.20592

摘要/Abstract

摘要： 以葡萄糖为原料，经乙酰化、选择性脱C1位乙酰基、转化成三氯乙酰亚胺酯、与受体醇偶联和脱保护5步反应合成了11种不同碳链长度的烷基β-D-吡喃葡萄糖苷。利用核磁共振、偏光显微镜和热失重分析法对其进行结构表征和性能测试。结果表明，当烷基β-D-吡喃葡萄糖苷疏水烷基链长n为 6~10时，均具有发泡和乳化性能，特别是正壬基β-D-吡喃葡萄糖苷(n=9)具有更加优异的发泡和乳化性能；当烷基β-D-吡喃葡萄糖苷疏水链的长度n≥7时，均具有热致液晶行为，特别是正十二烷基β-D-吡喃葡萄糖苷(n=12)和十四烷基β-D-吡喃葡萄糖苷(n=14)能够形成更加稳定的液晶态。

关键词: 葡萄糖, 烷基&, beta, -D-吡喃葡萄糖苷, 发泡, 乳化, 热致液晶

Abstract: Using D-glucose as precursor, eleven alkyl β-D-glucopyranosides with different carbon chain length were synthesized, via five consecutive steps including acetylation, selective deacetylation at the C1 position, conversion to trichloroacetimidate, coupling with acceptors alcohols and deprotection. Their structures and properties were characterized by NMR, polarization microscope(POM) and thermogravimetry(TG). The results show that alkyl β-D-glucopyranosides possess foaming and emulsifying capacities for those with chain length of hydrophobic aglycon n=6~10. Remarkably, n-nonyl-β-D-glucopyranoside(n=9) shows even superior foaming and emulsifying capacities. Meanwhile, when the chain length of hydrophobic aglycon(n) is greater than 7, all alkyl β-D-glucopyranosides exhibit thermotropic liquid crystalline behavior. Among them, n-dodecyl β-D-glucopyranoside with n=12 and n-tetradecyl β-D-glucopyranoside with n=14 can form more stable liquid crystal state.

Key words: glucose, alkyl &, beta, -D-glucopyranosides, foaming, emulsification, thermotropic liquid crystalline

中图分类号:

O621.2

刘灯峰, 陈朗秋, 李宏伟, 曾森, 旷娜, 田静. 烷基-β-D-吡喃葡萄糖苷的合成与性能[J]. 应用化学, DOI: 10.3724/SP.J.1095.2013.20592.

LIU Dengfeng, CHEN Langqiu*, LI Hongwei, ZENG Sen, KUANG Na, TIAN Jing. Syntheses and Properties of Alkyl β-D-Glucopyranosides[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20592.

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