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有机化学 ›› 2017, Vol. 37 ›› Issue (6): 1456-1462.DOI: 10.6023/cjoc201612034 上一篇    下一篇

研究论文

1，2-双十六烷基-3-甘油-磷酸乙醇胺的合成研究

张越, 张鹏涛, 于广利, 李春霞   

  1. 中国海洋大学医药学院 海洋药物教育部重点实验室 山东省糖科学与糖工程重点实验室 青岛 266003
  • 收稿日期:2016-12-09 修回日期:2017-02-13 发布日期:2017-02-17
  • 通讯作者: 李春霞 E-mail:lchunxia@ouc.edu.cn
  • 基金资助:

    国家自然科学基金委员会-山东省人民政府海洋科学研究中心联合（No.U1406402）、山东省泰山学者项目、海洋公益性行业科研专项（No.201405038）资助项目.

Synthesis of 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine

Zhang Yue, Zhang Pengtao, Yu Guangli, Li Chunxia   

  1. Key Laboratory of Glycoscience and Glycotechnology of Shandong Province, Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003
  • Received:2016-12-09 Revised:2017-02-13 Published:2017-02-17
  • Contact: 10.6023/cjoc201612034 E-mail:lchunxia@ouc.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China-Shandong Joint Fund for Marine Science Research Centers (No. U1406402), the Taishan Scholar Project Special Funds, and the Special Fund for Marine Scientific Research in the Public Interest (No. 201405038).

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1，2-双十六烷基-3-甘油-磷酸乙醇胺（DHPE）属于甘油磷脂的一种，在生物学方面具有广泛的应用.报道了化合物DHPE的合成，合成路线以（S）-（＋）-甘油醇缩丙酮、十六醇、乙醇胺为起始原料，得到了关键中间体1，2-双十六烷基甘油醇和Boc保护乙醇胺，然后通过Still-Gennari试剂将二者进行偶联，随后利用Horner-Wadsworth-Emmons反应高效的脱去磷脂上的乙酸甲酯基团，最终经过8步反应，以32%的总收率得到目标化合物DHPE.

关键词: DHPE, 甘油磷脂, 合成, Horner-Wadsworth-Emmons反应

1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine (DHPE) is one type of glycerophospholipids, and it has a wide range of application in biology. A new and efficient method was developed to synthesis DHPE using (S)-2,2-dimethyl-1,3-dioxolane-4-methanol, hexadecanol and ethanolamine as starting materials. 1,2-Dihexadecyl-sn-glycerol and N-Boc-etha-nolamine were synthesized as two key intermediates, which were coupled under condition of Still-Gennari reagent. Then Horner-Wadsworth-Emmons reaction condition was applied to deprotect methyl acetate group of glycerophospholipid efficiently. The target compound DHPE was obtained in 32% overall yield by 8 steps.

Key words: DHPE, glycerophospholipids, synthesis, Horner-Wadsworth-Emmons reactions