(8S,9R)-13-O-acetyl-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid | 565220-29-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (8S,9R)-13-O-acetyl-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
• CAS: 565220-29-3
• 化学式: C₄₂H₆₂O₉
• 分子量: 710.949
• InChiKey: LPHRLONDELMYEA-OEBVRLFHSA-N

物化性质

• 沸点：
  784.3±55.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120.75
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (8S,9R)-13-O-acetyl-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
  参考文献：
  名称：

  Computer-assisted design and lactonization of model seco-acid derivatives of lankanolide

  摘要：

  In some cases, seco-acid derivatives (a precursor of macrolactone) did not cyclize to form the corresponding macrolactone. To design easily cyclizable seco-acid derivatives of lanaknolide, the conformation of several model seco-acids was calculated, and lactonization experiments of the seco-acids prepared from oleandomycin were carried out to elucidate the efficiency of the cyclization of the model seco-acid. The easily cyclable seco-acid was designed to be C8 exomethylene derivative of lankanolide seco-acid. On the other hand, seco-acid derivative having tertiary alcohol at C8 was predicted not to cyclize to form macrolactone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.061
• 作为产物：
  描述：

  (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 jones reagent 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 、 丙酮 为溶剂， 反应 73.33h， 生成 (8S,9R)-13-O-acetyl-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
  参考文献：
  名称：

  The first stereoselective total synthesis of lankanolide. Part 1: Computer-assisted design and lactonization of model seco-acid derivatives

  摘要：

  To design easily cyclizable seco-acid derivatives of lankanolide, the conformation of several model seco-acids was calculated and the lactonization experiments of the seco-acids were carried out to elucidate the efficiency of the cyclization of the model seco-acid. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00954-7