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Citation: 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, ;2013, 30(10): 1120-1126. doi: 10.3724/SP.J.1095.2013.20592 shu

Syntheses and Properties of Alkyl β-D-Glucopyranosides

College of Chemistry, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Xiangtan University, Xiangtan 411105, China

Received Date: 18 December 2012
Revised Date: 24 January 2013

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.
- glucose,
- alkyl β-D-glucopyranosides,
- foaming,
- emulsification,
- thermotropic liquid crystalline
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