(2R,3R,6S)-7-(benzyloxy)-2-(but-3-enyl)-6-methylheptane-1,3-diol | 1408299-02-4

• 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: (2R,3R,6S)-7-(benzyloxy)-2-(but-3-enyl)-6-methylheptane-1,3-diol
• CAS: 1408299-02-4
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: BFBQDTOHJTVIDU-QXAKKESOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  22.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,6S)-7-(benzyloxy)-2-(but-3-enyl)-6-methylheptane-1,3-diol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氨 、 lithium 、 对甲苯磺酸 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006
• 作为产物：
  描述：

  (S)-5-(benzyloxy)-4-methylpentan-1-ol 在 sodium tetrahydroborate 、 三氟甲磺酸二丁硼 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.67h， 生成 (2R,3R,6S)-7-(benzyloxy)-2-(but-3-enyl)-6-methylheptane-1,3-diol
  参考文献：
  名称：

  Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid

  摘要：

  A flexible and efficient asymmetric route to the synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W has been accomplished from commercially available 4-pentenoic acid. The successful generation of stereocenters was achieved by utilizing an Evans' chiral auxiliary-based alkylation and aldol reaction. Other key reactions such as a Julia-Kocienski olefination, Kita's macrolactonization, ring closing metathesis (RCM) reaction, and Yamaguchi's esterification were significant for the construction of the macrolactone cores. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.006