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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1716 - 1724

DOI: https://doi.org/10.6023/cjoc201911025

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

  • Chen Zili ,
  • Li Peixia ,
  • Liu Weitong ,
  • Zhuang Zhe ,
  • Wu Yuanyuan ,
  • Zhao Hanqing ,
  • Zhang Jianjun
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  • 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 date: 2019-11-20

  Revised date: 2020-01-22

  Online 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).

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Abstract

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

Cite this article

Chen Zili , Li Peixia , Liu Weitong , Zhuang Zhe , Wu Yuanyuan , Zhao Hanqing , Zhang Jianjun . High Efficiency Synthesis of the Tetrasccharide Repeating Unit in Azospirillum brasilense Strains Sp246 Based on Silica Gel Supported Perchloric Acid (HClO4-SiO2)[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1716 -1724 . DOI: 10.6023/cjoc201911025

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