(2R,3E)-2-(methoxymethoxy)-3-octadecenoic acid | 131622-90-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3E)-2-(methoxymethoxy)-3-octadecenoic acid
• 英文别名: (E,2R)-2-(methoxymethoxy)octadec-3-enoic acid
• CAS: 131622-90-7
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: VLKWUNCVGSDQPK-BMINWGARSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  458.7±30.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3E)-2-(methoxymethoxy)-3-octadecenoic acid 在 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙硫醇 为溶剂， 反应 15.67h， 生成 methyl (2'R,3'E)-2'-hydroxyoctadec-3'-enoate
  参考文献：
  名称：

  First Total Synthesis of Symbioramide, a Novel Ca²⁺-ATPase Activator fromSymbiodiniumsp.

  摘要：

  描述了symbioramide (1) 的首次全合成，并同时确定了1的完整立体结构为(2S,3R,2′R,3′E)-N-(2′-羟基-3′-十八烯酰)-二氢鞘氨醇。

  DOI：

  10.1246/cl.1990.1407
• 作为产物：
  描述：

  pentadecyltriphenylphosphonium bromide 在 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 二苯二硫醚 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 (2R,3E)-2-(methoxymethoxy)-3-octadecenoic acid
  参考文献：
  名称：

  Total Syntheses of Symbioramide Derivatives from l-Serine and Their Antileukemic Activities

  摘要：

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.

  DOI：

  10.1021/jo0206824

文献信息

• First Total Synthesis of Symbioramide, a Novel Ca²⁺-ATPase Activator from<i>Symbiodinium</i>sp.
  作者：Masako Nakagawa、Jun Yoshida、Tohru Hino

  DOI：10.1246/cl.1990.1407

  日期：1990.8

  The first total synthesis of symbioramide (1) is described and simultaneously established the complete stereostructure of 1 to be (2S,3R,2′R,3′E)-N-(2′-hydroxy-3′-octadecenoyl)-dihydrosphingosine.

  描述了symbioramide (1) 的首次全合成，并同时确定了1的完整立体结构为(2S,3R,2′R,3′E)-N-(2′-羟基-3′-十八烯酰)-二氢鞘氨醇。
• NAKAGAWA, MASAKO;YOSHIDA, JUN;HINO, TOHRU, CHEM. LETT.,(1990) N, C. 1407-1410
  作者：NAKAGAWA, MASAKO、YOSHIDA, JUN、HINO, TOHRU

  DOI：——

  日期：——
• Yoshida, Jun; Nakagawa, Masako; Seki, Hiroko, Journal of the Chemical Society. Perkin transactions I, 1992, # 3, p. 343 - 350
  作者：Yoshida, Jun、Nakagawa, Masako、Seki, Hiroko、Hino, Tohru

  DOI：——

  日期：——
• Total Syntheses of Symbioramide Derivatives from <scp>l</scp>-Serine and Their Antileukemic Activities
  作者：Hideki Azuma、Ryoko Takao、Hayato Niiro、Keiji Shikata、Seizo Tamagaki、Taro Tachibana、Kenji Ogino

  DOI：10.1021/jo0206824

  日期：2003.4.1

  Naturally occurring symbioramide, (2S,3R,2'R,3'E)-N-(2'-hydroxy-3'-octadecenoyl)-dihydrosphingosine la, was synthesized from D-erythro-dihydrosphingosine (amino part, 2) and (2R,3E)-2-hydroxy-3-octadecenoic acid (acid part, 3a), both of which were prepared from L-serine. Its diastereomer, (2S,3R,2'S,3'E)-1b, having an enantiomer of the unnatural-type acid part that was prepared from D-mannitol, and its corresponding (Z)-isomers, (2S,3R,2R,3'Z)-1c and (2S,3R,2'S,3'Z)-1d, were also prepared. The antileukemic activities of 1a-d against HL-60 and L-1210 cells were appreciated by a MTT assay. None of the four symbioramide derivatives showed antileukemic activities in HL-60 cells. In L-1210 cells, all the symbioramide derivatives showed moderate antileukemic activities. Compound 1d had the most effective activity against L-1210 cells among the four derivatives. The data suggest that unnatural types of (2'S)-isomers of acid parts are more active than those of (2R)-isomers.