Syntheses and Properties of Alkyl β-D-Glucopyranosides

doi:10.3724/SP.J.1095.2013.20592

Chinese Journal of Applied Chemistry

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Syntheses and Properties of Alkyl β-D-Glucopyranosides

LIU Dengfeng, CHEN Langqiu^*, LI Hongwei, ZENG Sen, KUANG Na, TIAN Jing

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

Received:2012-12-18 Revised:2013-01-23 Published:2013-10-10 Online:2013-10-10

Abstract

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

CLC Number:

O621.2

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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Syntheses and Properties of Alkyl β-D-Glucopyranosides

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