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端基含甲基保护羧基的三半乳糖苷的设计和合成

Design and synthesis of tris(1-thiogalactopyranoside) having a methyl-protected carboxy group at the aglycon terminals

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【作者】 蔡春蒋庆琳张国尧吴勇

【Author】 CAI Chun~(1,2),JIANG Qing-lin~1,ZHANG Guo-yao~1,WU Yong~(1*)(1.West China School of Pharmacy,Sichuan University,Chengdu 610041,China;2.Analytic Center,Guangdong Medical College,Zhanjiang 524023,China)

【机构】 四川大学华西药学院四川大学华西药学院 四川成都610041广东医学院分析中心广东湛江524023四川成都610041

【摘要】 目的合成端基含羧基衍生功能基的三半乳糖苷。方法以季戊四醇为起始原料,经加成、醇解、还原、磺酰化,再与已知的2-S-(2,3,4,6)-四-O-乙酰基-β-D-半乳吡喃糖基-2-异硫脲氢溴酸盐作用,共5步反应,制得三(ω-2,3,4,6-四-O-乙酰基-β-D-半乳吡喃糖硫基丙氧甲基)(ω-甲氧甲酰乙氧甲基)甲烷。结果和结论合成制得目标化合物,并经1HNMR,IR和MS确证结构。

【Abstract】 OBJECTIVE To synthesize Tris-1-thiogalactopyranoside having a methyl-protected carboxy group at the aglycon terminals.METHODS Starting from quaternary pentanetetraol,followed by addition,alcoholysis,reduction,sulfonation and final straightforward condensation with the available versatile saccharide reagent,2-S-(2,3,4,6)-tetra-O-acetyl-β-D-galactopyranosyl-2-thiopseudourea hydrobromide,the title compound tris(ω-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthiopropoxymethyl)(ω-methoxycarbonylethoxymethyl)methane has been synthesized via 5 designed reaction steps.RESULTS and CONCLUSION The title compound was synthesized and confirmed by 1H-NMR,IR,and MS.

【基金】 教育部博士点基金资助项目(批准号:20050610085)
  • 【文献出处】 华西药学杂志 ,West China Journal of Pharmaceutical Sciences , 编辑部邮箱 ,2006年03期
  • 【分类号】R914
  • 【被引频次】1
  • 【下载频次】176
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