(9R)-3,5:9,11-bis-O-isopropylidene-8,8a-deoxa-9-dihydrooleandonolide seco acid | 565220-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (9R)-3,5:9,11-bis-O-isopropylidene-8,8a-deoxa-9-dihydrooleandonolide seco acid
• 英文别名: (2R)-2-[(4S,5R,6S)-6-[(2S)-4-[(4R,5R,6S)-6-[(2S,3R)-3-hydroxybutan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]pent-4-en-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]propanoic acid
• CAS: 565220-22-6
• 化学式: C₂₆H₄₆O₇
• 分子量: 470.647
• InChiKey: MFANOUODUXSHEI-QUJASINTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (9R)-3,5:9,11-bis-O-isopropylidene-8,8a-deoxa-9-dihydrooleandonolide seco acid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 62.5h， 生成 (2R,3S,4R,5S,6S,9R,10R,11S,12S,13R)-3,5:9,11-bis(isopropylidenedioxy)-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide
  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：

  (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-9,11-dihydroxy-3,5-(isopropylidenedioxy)-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 8.25h， 生成 (9R)-3,5:9,11-bis-O-isopropylidene-8,8a-deoxa-9-dihydrooleandonolide 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

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.