Home

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
1. [1]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
2. [2]
  Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
3. [3]
  Yuhang Jiang , Weijie Liu , Jiaqi Cai , Jiayue Chen , Yanping Ren , Pingping Wu , Liulin Yang . A Journey into the Science and Art of Sugar: “Dispersion of Light and Optical Rotation of Matter” Science Popularization Experiment. University Chemistry, 2024, 39(9): 288-294. doi: 10.12461/PKU.DXHX202401054
4. [4]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
5. [5]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
6. [6]
  Yang Lv , Yingping Jia , Yanhua Li , Hexiang Zhong , Xinping Wang . Integrating the Ideological Elements with the “Chemical Reaction Heat” Teaching. University Chemistry, 2024, 39(11): 44-51. doi: 10.12461/PKU.DXHX202402059
7. [7]
  Xiyuan Su , Zhenlin Hu , Ye Fan , Xianyuan Liu , Xianyong Lu . Change as You Want: Multi-Responsive Superhydrophobic Intelligent Actuation Material. University Chemistry, 2024, 39(5): 228-237. doi: 10.3866/PKU.DXHX202311059
8. [8]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
9. [9]
  Limei CHEN , Mengfei ZHAO , Lin CHEN , Ding LI , Wei LI , Weiye HAN , Hongbin WANG . Preparation and performance of paraffin/alkali modified diatomite/expanded graphite composite phase change thermal storage material. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 533-543. doi: 10.11862/CJIC.20230312
10. [10]
  Mingxin LU , Liyang ZHOU , Xiaoyu XU , Xiaoying FENG , Hui WANG , Bin YAN , Jie XU , Chao CHEN , Hui MEI , Feng GAO . Preparation of La-doped lead-based piezoelectric ceramics with both high electrical strain and Curie temperature. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 329-338. doi: 10.11862/CJIC.20240206
11. [11]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
12. [12]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
13. [13]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
14. [14]
  Yukun Xing , Xiaoyu Xie , Fangfang Chen . A Sunlit Gift: Vitamin D. University Chemistry, 2024, 39(9): 28-34. doi: 10.12461/PKU.DXHX202402006
15. [15]
  Yuexi Guo , Zhaoyang Li , Jingwei Dai . Charlie and the 3D Printing Chocolate Factory. University Chemistry, 2024, 39(9): 235-242. doi: 10.3866/PKU.DXHX202309067
16. [16]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
17. [17]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
18. [18]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
19. [19]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
20. [20]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(217)
HTML views(17)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return