Chinese Journal of Organic Chemistry >
Synthesis of 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine
Received date: 2016-12-09
Revised date: 2017-02-13
Online published: 2017-02-17
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).
1,2-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
Zhang Yue , Zhang Pengtao , Yu Guangli , Li Chunxia . Synthesis of 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine[J]. Chinese Journal of Organic Chemistry, 2017 , 37(6) : 1456 -1462 . DOI: 10.6023/cjoc201612034
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