(1-octadecanoyloxy-3-undec-10-enoyloxypropan-2-yl) 17-[4-[3-[4-[(Z)-17-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoctadec-9-enoyl]piperazin-1-yl]-3-oxopropyl]triazol-1-yl]octadecanoate | 1205678-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (1-octadecanoyloxy-3-undec-10-enoyloxypropan-2-yl) 17-[4-[3-[4-[(Z)-17-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoctadec-9-enoyl]piperazin-1-yl]-3-oxopropyl]triazol-1-yl]octadecanoate
• CAS: 1205678-65-4
• 化学式: C₈₉H₁₅₉N₅O₁₉
• 分子量: 1603.26
• InChiKey: FPGOSRUCRVQTNH-XEUKRVBGSA-N

反应信息

• 作为产物：
  描述：

  (1-Octadecanoyloxy-3-undec-10-enoyloxypropan-2-yl) 17-azidooctadecanoate 、 (Z)-17-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-(4-pent-4-ynoylpiperazin-1-yl)octadec-9-en-1-one 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以94%的产率得到(1-octadecanoyloxy-3-undec-10-enoyloxypropan-2-yl) 17-[4-[3-[4-[(Z)-17-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoctadec-9-enoyl]piperazin-1-yl]-3-oxopropyl]triazol-1-yl]octadecanoate
  参考文献：
  名称：

  可点击的脂质：叠氮基和炔基脂肪酸以及三酰基甘油

  摘要：

  AbstractHydroxy fatty acids (FAs), which were isolated from glycolipids that can be prepared fermentatively from fats and oils, have been synthetically modified to contain azide and alkyne functional groups. These particular functional groups were chosen because they can participate in a copper‐catalyzed reaction that combines them to form a 1,4‐triazole, known as a “click” reaction, which has been widely used in a variety of fields but remains underutilized in FA chemistry. Depending on the starting hydroxy FA, these groups can be close to the carboxy unit (using 3‐hydroxydecanoate) and hence the polar glycerol group, or distant from it (using 17‐hydroxyoctadecanoate). These structural alternatives will impart different properties to the triacylglycerols that are subsequently prepared from the modified FA. Finally, the click reaction was used to conjugate triacylglycerols to each other and to other molecules such as a glycolipid or a protected amine.

  DOI：

  10.1007/s11746-009-1442-z