Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1716-1724.DOI: 10.6023/cjoc201911025 Previous Articles     Next Articles


陈自力a, 李培霞a, 刘伟童a, 庄喆a, 武源源a, 赵汗青a, 张建军b   

  1. a 北京农学院 农业农村部华北都市农业重点实验室 北京 102206;
    b 中国农业大学理学院 北京 100193
  • 收稿日期:2019-11-20 修回日期:2020-01-22 发布日期:2020-02-15
  • 通讯作者: 赵汗青, 张建军;
  • 基金资助:

High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO4-SiO2)

Chen Zilia, Li Peixiaa, Liu Weitonga, Zhuang Zhea, Wu Yuanyuana, Zhao Hanqinga, Zhang Jianjunb   

  1. a Key Laboratory for Northern Urban Agriculture of Ministry of Agriculture and Rural Affairs, Beijing University of Agriculture, Beijing 102206;
    b School of Science, China Agricultural University, Beijing 100193
  • Received:2019-11-20 Revised:2020-01-22 Published:2020-02-15
  • Supported by:
    Project supported by the Natural Science Foundation of Beijing City (No. 2194072), the National Natural Science Foundation of China (No. 21772230), the General Plan of Beijing Education Commission (No. KM201710020003), the Seed Funding of Beijing Jinqiao Project (No. JQ18029), the Youth Foundation of Beijing University of Agriculture (No. SXQN201801), the Research Fund for Academic Degree & Graduate Education of Beijing University of Agriculture (No. 2019YJS028) and the Connotation Development Quota Scientific Research Training for College Students of Beijing University of Agriculture (No. KX2019001).

A natural tetrasaccharide of α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-[β-D-Glup-(1→4)-]α-L-Rhap was synthesized via [2+2] assembly from 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate, p-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside, 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate and p-methoxyphenyl 2,3-O-isopro-pyl-α-L-rhamnopyranoside. This tetrasaccharide is a repeating unit of the lipopolisaccharides of the nitrogen fixing bacterium Azospirillum brasilense Sp246. In the reaction of the synthesis unit, silica gel loaded perchloric acid (HClO4-SiO2) was used as acid catalyst, and triethylsilyl group was used as selective protective group to construct a fully protected tetrasaccharide. The synthetic route is short, the reagents are few, and the post-processing is simple. The total yield of target tetrasaccharide is 23% based on L-rhamnose. The structures of the tetrasaccharide were confirmed by 1H NMR, 13C NMR, HRMS and IR spectra.

Key words: rhamnose, silica gel supported perchloric acid (HClO4-SiO2), Azospirillum brasilense, oligosaccharide synthesis