(3R,4E,24E,26R)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol | 1312225-41-4

• 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: (3R,4E,24E,26R)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol
• 英文别名: miyakosyne A；(3R,4E,14R,24E,26R)-14-methyloctacosa-4,24-dien-1,27-diyne-3,26-diol
• CAS: 1312225-41-4
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: VAEFGKZDLREYOM-XRLFQHQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4E,24E,26R)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol 、 (1R,2R)-2-(蒽-2,3-二甲酰亚胺基)环己甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 (3R,4E,14R,24E,26R)-14-methyloctacosa-4,24-dien-1,27-diyne-3,26-diyl (1R,1'R,2R,2'R)-bis(2-(1,3-dioxo-1,3-dihydro-2H-naphtho[2,3-f]isoindol-2-yl)cyclohexane-1-carboxylate)
  参考文献：
  名称：

  Chemoenzymatic synthesis and HPLC analysis of the stereoisomers of miyakosyne A [(4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol], a cytotoxic metabolite of a marine sponge Petrosia sp., to determine the absolute configuration of its major component as 3R,14R,26R

  摘要：

  Six samples [(3R,14R,26R)-, (3R,14S,26R)-, (3S,14R,26S)-, and (3S,14S,26S)-1, a mixture of (3R,14R,26S)and (3S,14R,26R)-1, and a mixture of (3R,145,26S)- and (3S,14S,26R)-1] of miyakosyne A [1, (4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol] were synthesized starting from the enantiomers of citronellal (2), employing olefin cross metathesis and R-selective asymmetric acetylation of a stereoisomeric mixture of acetylenic alcohols with vinyl acetate and lipase PS as key reactions. Separation of the eight stereoisomer of 1 by reversed phase HPLC at 56 C was achieved after their esterification with (1R,2R)-2-(anthracene-2,3-dicarboximido)cyclohexanecarboxylic acid (16), and the natural miyakosyne A was found to be a mixture of 95.7% of (3R,14R,26R)-1 and 4.3% of (3R,14S,26R)-1. This is different from the (3R,145,26R)-configuration of 1 as tentatively assigned by X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.045
• 作为产物：
  描述：

  (3R,4E,14R,24E,26R)-14-methyl-1,28-bis(trimethylsilyl)octacosa-4,24-dien-1,27-diyne-3,26-diyl diacetate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以51%的产率得到(3R,4E,24E,26R)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis and HPLC analysis of the stereoisomers of miyakosyne A [(4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol], a cytotoxic metabolite of a marine sponge Petrosia sp., to determine the absolute configuration of its major component as 3R,14R,26R

  摘要：

  Six samples [(3R,14R,26R)-, (3R,14S,26R)-, (3S,14R,26S)-, and (3S,14S,26S)-1, a mixture of (3R,14R,26S)and (3S,14R,26R)-1, and a mixture of (3R,145,26S)- and (3S,14S,26R)-1] of miyakosyne A [1, (4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol] were synthesized starting from the enantiomers of citronellal (2), employing olefin cross metathesis and R-selective asymmetric acetylation of a stereoisomeric mixture of acetylenic alcohols with vinyl acetate and lipase PS as key reactions. Separation of the eight stereoisomer of 1 by reversed phase HPLC at 56 C was achieved after their esterification with (1R,2R)-2-(anthracene-2,3-dicarboximido)cyclohexanecarboxylic acid (16), and the natural miyakosyne A was found to be a mixture of 95.7% of (3R,14R,26R)-1 and 4.3% of (3R,14S,26R)-1. This is different from the (3R,145,26R)-configuration of 1 as tentatively assigned by X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.045

文献信息

• Chemoenzymatic synthesis and HPLC analysis of the stereoisomers of miyakosyne A [(4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol], a cytotoxic metabolite of a marine sponge Petrosia sp., to determine the absolute configuration of its major component as 3R,14R,26R
  作者：Kenji Mori、Kazuaki Akasaka、Shigeki Matsunaga

  DOI：10.1016/j.tet.2013.11.045

  日期：2014.1

  Six samples [(3R,14R,26R)-, (3R,14S,26R)-, (3S,14R,26S)-, and (3S,14S,26S)-1, a mixture of (3R,14R,26S)and (3S,14R,26R)-1, and a mixture of (3R,145,26S)- and (3S,14S,26R)-1] of miyakosyne A [1, (4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol] were synthesized starting from the enantiomers of citronellal (2), employing olefin cross metathesis and R-selective asymmetric acetylation of a stereoisomeric mixture of acetylenic alcohols with vinyl acetate and lipase PS as key reactions. Separation of the eight stereoisomer of 1 by reversed phase HPLC at 56 C was achieved after their esterification with (1R,2R)-2-(anthracene-2,3-dicarboximido)cyclohexanecarboxylic acid (16), and the natural miyakosyne A was found to be a mixture of 95.7% of (3R,14R,26R)-1 and 4.3% of (3R,14S,26R)-1. This is different from the (3R,145,26R)-configuration of 1 as tentatively assigned by X-ray analysis. (C) 2013 Elsevier Ltd. All rights reserved.