(4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol | 1567376-26-4

• 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: (4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol
• 英文别名: (4R,5Z,7R,8S,9S,10S)-7,8,9,10-tetrakis(phenylmethoxy)undeca-1,5-dien-4-ol
• CAS: 1567376-26-4
• 化学式: C₃₉H₄₄O₅
• 分子量: 592.775
• InChiKey: AQFIQDSCWZLUDV-LAHJRMLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-6-((1Z,3R,4S,5S,6S)-3,4,5,6-tetrakis(benzyloxy)hept-1-enyl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-boronolide, (+)-anamarine, 8-epi-spicegerolide

  摘要：

  A stereoselective total synthesis of the naturally occurring cytotoxic lactones (+)-boronolide, (+)-anamarine, and 8-epi-spicigerolide is described. D-Xylose has been used as a chiral source to construct the four contiguous oxygenated stereogenic centers of target molecules. The diastereoselective allylation was performed using Brown's protocol and the lactone moiety was prepared by ring closing metathesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.061
• 作为产物：
  描述：

  在 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 (4R,5R,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol 、 (4S,5Z,7R,8S,9S,10S)-7,8,9,10-tetrakis(benzyloxy)undeca-1,5-dien-4-ol
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-boronolide, (+)-anamarine, 8-epi-spicegerolide

  摘要：

  A stereoselective total synthesis of the naturally occurring cytotoxic lactones (+)-boronolide, (+)-anamarine, and 8-epi-spicigerolide is described. D-Xylose has been used as a chiral source to construct the four contiguous oxygenated stereogenic centers of target molecules. The diastereoselective allylation was performed using Brown's protocol and the lactone moiety was prepared by ring closing metathesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.061

文献信息

• Stereoselective total synthesis of (+)-boronolide, (+)-anamarine, 8-epi-spicegerolide
  作者：B.V. Subba Reddy、V. Veerabhadra Reddy、K. Praneeth

  DOI：10.1016/j.tetlet.2013.12.061

  日期：2014.2

  A stereoselective total synthesis of the naturally occurring cytotoxic lactones (+)-boronolide, (+)-anamarine, and 8-epi-spicigerolide is described. D-Xylose has been used as a chiral source to construct the four contiguous oxygenated stereogenic centers of target molecules. The diastereoselective allylation was performed using Brown's protocol and the lactone moiety was prepared by ring closing metathesis. (C) 2013 Elsevier Ltd. All rights reserved.