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

doi:10.6023/cjoc201612034

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1456-1462.DOI: 10.6023/cjoc201612034 Previous Articles Next Articles

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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

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

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).

1. Synthesis of 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine.PDF(620KB)

Abstract

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

Cite this article

Zhang Yue, Zhang Pengtao, Yu Guangli, Li Chunxia. Synthesis of 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine[J]. Chin. J. Org. Chem., 2017, 37(6): 1456-1462.

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1，2-双十六烷基-3-甘油-磷酸乙醇胺的合成研究

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

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