(E,6S)-6-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]hex-2-ene-1,6-diol | 1195988-19-2

• 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: (E,6S)-6-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]hex-2-ene-1,6-diol
• CAS: 1195988-19-2
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: FOJKBQQBVRITKY-RLRMVEOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,6S)-6-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]hex-2-ene-1,6-diol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 作用下， 以 异辛烷 、 二氯甲烷 为溶剂， 反应 20.0h， 以88%的产率得到(1R)-1-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]ethane-1,2-diol
  参考文献：
  名称：

  Toward the Total Synthesis of Goniodomin A, An Actin-Targeting Marine Polyether Macrolide: Convergent Synthesis of the C15−C36 Segment

  摘要：

  Stereoselective convergent synthesis of the C15-C36 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved. The present synthesis features palladium(0)-catalyzed, copper(I)-mediated Liebeskind-Srogl cross-coupling as the fragment assembly process.

  DOI：

  10.1021/ol902217q
• 作为产物：
  描述：

  (1S)-1-((2R,6S)-6-((benzyloxy)methyl)-5,6-dihydro-2H-pyran-2-yl)-4,5-dihydroxypentyl acetate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 以98%的产率得到(E,6S)-6-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]hex-2-ene-1,6-diol
  参考文献：
  名称：

  Toward the Total Synthesis of Goniodomin A, An Actin-Targeting Marine Polyether Macrolide: Convergent Synthesis of the C15−C36 Segment

  摘要：

  Stereoselective convergent synthesis of the C15-C36 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved. The present synthesis features palladium(0)-catalyzed, copper(I)-mediated Liebeskind-Srogl cross-coupling as the fragment assembly process.

  DOI：

  10.1021/ol902217q

文献信息

• Toward the Total Synthesis of Goniodomin A, An Actin-Targeting Marine Polyether Macrolide: Convergent Synthesis of the C15−C36 Segment
  作者：Tomoyuki Saito、Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1021/ol902217q

  日期：2009.11.19

  Stereoselective convergent synthesis of the C15-C36 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved. The present synthesis features palladium(0)-catalyzed, copper(I)-mediated Liebeskind-Srogl cross-coupling as the fragment assembly process.