Citation: 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 shu

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

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

Corresponding author: Zhao Hanqing, zhaohanqing@bua.edu.cn Zhang Jianjun, zhangjianjun@cau.edu.cn
Received Date: 20 November 2019
Revised Date: 22 January 2020
Available Online: 14 February 2020
Fund Project: the Youth Foundation of Beijing University of Agriculture SXQN201801the Connotation Development Quota Scientific Research Training for College Students of Beijing University of Agriculture KX2019001the Natural Science Foundation of Beijing City 2194072the Research Fund for Academic Degree & Graduate Education of Beijing University of Agriculture 2019YJS028the National Natural Science Foundation of China 21772230the Seed Funding of Beijing Jinqiao Project JQ18029the General Plan of Beijing Education Commission KM201710020003Project 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)

Figures(5)

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.
- rhamnose,
- silica gel supported perchloric acid (HClO₄-SiO₂),
- Azospirillum brasilense,
- oligosaccharide synthesis
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

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