(+)-(14R,15S,E)-14-(4-methoxybenzyloxy)-1,11,11-trimethyl-15-pentyl-14,15-dihydro-5H-benzo[b]-10,12-dioxo[1,2-j][1,5]dioxacycloundecin-17(9H)-one | 1449522-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(14R,15S,E)-14-(4-methoxybenzyloxy)-1,11,11-trimethyl-15-pentyl-14,15-dihydro-5H-benzo[b]-10,12-dioxo[1,2-j][1,5]dioxacycloundecin-17(9H)-one
• 英文别名: (11S,12R,13E)-12-[(4-methoxyphenyl)methoxy]-7,19,19-trimethyl-11-pentyl-2,10,18,20-tetraoxatetracyclo[13.8.0.03,8.016,21]tricosa-1(15),3,5,7,13,16(21),22-heptaen-9-one
• CAS: 1449522-88-6
• 化学式: C₃₅H₄₀O₇
• 分子量: 572.698
• InChiKey: DDPRGKKYUYPTDK-UMEKXAKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-(14R,15S,E)-14-(4-methoxybenzyloxy)-1,11,11-trimethyl-15-pentyl-14,15-dihydro-5H-benzo[b]-10,12-dioxo[1,2-j][1,5]dioxacycloundecin-17(9H)-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 以77%的产率得到(11S,12R,13E)-17-hydroxy-16-(hydroxymethyl)-12-[(4-methoxyphenyl)methoxy]-7-methyl-11-pentyl-2,10-dioxatricyclo[13.4.0.03,8]nonadeca-1(15),3,5,7,13,16,18-heptaen-9-one
  参考文献：
  名称：

  Enantioselective synthesis of (+)-aspercyclide A

  摘要：

  An efficient synthesis of the natural IgE-Fc epsilon RI PPI inhibitor (+)-aspercyclide A (1) was achieved through the use of a Krische iridium-catalyzed diastereo- and enantioselective alkoxyallylation to form the key mono-protected anti-diol intermediate 4, in high optical purity. A derivative of the natural product (15), containing an oxathiazine dioxide ring in place of the ring-A hydroxyaldehyde unit has also been prepared and found to display comparable ELISA activity to the parent compound, indicating that the aldehyde group is not the key determinant of activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.038
• 作为产物：
  描述：

  (3R,4S)-3-benzoyloxynon-1-en-4-ol 在 copper(I) oxide 、 bis(acetylacetonato)palladium(II) 、 copper(l) iodide 、 1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 、 N,N-二甲基乙二胺 、 三乙胺 、 sodium iodide 、 silver(I) iodide 、 copper(II) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 128.0h， 生成 (+)-(14R,15S,E)-14-(4-methoxybenzyloxy)-1,11,11-trimethyl-15-pentyl-14,15-dihydro-5H-benzo[b]-10,12-dioxo[1,2-j][1,5]dioxacycloundecin-17(9H)-one
  参考文献：
  名称：

  Enantioselective synthesis of (+)-aspercyclide A

  摘要：

  An efficient synthesis of the natural IgE-Fc epsilon RI PPI inhibitor (+)-aspercyclide A (1) was achieved through the use of a Krische iridium-catalyzed diastereo- and enantioselective alkoxyallylation to form the key mono-protected anti-diol intermediate 4, in high optical purity. A derivative of the natural product (15), containing an oxathiazine dioxide ring in place of the ring-A hydroxyaldehyde unit has also been prepared and found to display comparable ELISA activity to the parent compound, indicating that the aldehyde group is not the key determinant of activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.038

文献信息

• Enantioselective synthesis of (+)-aspercyclide A
  作者：Jimmy J.P. Sejberg、Lucy D. Smith、Robin J. Leatherbarrow、Andrew J. Beavil、Alan C. Spivey

  DOI：10.1016/j.tetlet.2013.07.038

  日期：2013.9

  An efficient synthesis of the natural IgE-Fc epsilon RI PPI inhibitor (+)-aspercyclide A (1) was achieved through the use of a Krische iridium-catalyzed diastereo- and enantioselective alkoxyallylation to form the key mono-protected anti-diol intermediate 4, in high optical purity. A derivative of the natural product (15), containing an oxathiazine dioxide ring in place of the ring-A hydroxyaldehyde unit has also been prepared and found to display comparable ELISA activity to the parent compound, indicating that the aldehyde group is not the key determinant of activity. (C) 2013 Elsevier Ltd. All rights reserved.