(8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid | 714217-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid
• 英文别名: (2R)-2-[(2S,4S,5R,6S)-6-[(2S,4S)-4-hydroxy-4-[(2S,4R,5R,6S)-6-[(2S,3R)-3-hydroxybutan-2-yl]-5-methyl-2-(2,4,6-trimethylphenyl)-1,3-dioxan-4-yl]pentan-2-yl]-5-methyl-2-(2,4,6-trimethylphenyl)-1,3-dioxan-4-yl]propanoic acid
• CAS: 714217-50-2
• 化学式: C₄₀H₆₀O₈
• 分子量: 668.912
• InChiKey: CSSUKVLXSYAVKW-ZMWIGOBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (8S,9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidenedioxy)-8-hydroxy-8,8a-deoxa-9-dihydro-oleandonolide seco-acid 、 三甲基硅烷化重氮甲烷 在 甲醇 作用下， 以 正己烷 、 苯 为溶剂， 反应 1.0h， 以90%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 methyl ester
  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：

  2-(二甲氧基甲基)-1,3,5-三甲基苯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 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 、 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 、 丙酮 为溶剂， 反应 97.33h， 生成 (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：

  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

文献信息

• The first stereoselective total synthesis of lankanolide. Part 1: Computer-assisted design and lactonization of model seco-acid derivatives
  作者：Tatsuo Hamada、Yukinari Kobayashi、Mitsugu Kiyokawa、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(03)00954-7

  日期：2003.6

  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.
• Computer-assisted design and lactonization of model seco-acid derivatives of lankanolide
  作者：Tatsuo Hamada、Mitsugu Kiyokawa、Yukinari Kobayashi、Toshikazu Yoshioka、Junichiro Sano、Osamu Yonemitsu

  DOI：10.1016/j.tet.2004.03.061

  日期：2004.5

  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.