(8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 3,5-acetonide | 116417-71-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 3,5-acetonide
• 英文别名: (1S,2R,5R,6R,7S,8R,10S,12S,13S,17R)-7,10-dihydroxy-10-(iodomethyl)-2,5,6,8,12,15,15,17-octamethyl-4,14,16-trioxabicyclo[11.3.1]heptadecane-3,9-dione
• CAS: 116417-71-1
• 化学式: C₂₃H₃₉IO₇
• 分子量: 554.463
• InChiKey: RBHICHBTBZTYCS-DLDIFSOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  31.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 3,5-acetonide 在 chromium dichloride 、 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 camphor-10-sulfonic acid 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 、 苯 为溶剂， 反应 31.42h， 生成 (9R)-3,5-O-isopropylidene-9,11-O-(2,4,6-trimethylbenzylidene)-8,8a-deoxa-9-dihydrooleandonolide 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：

  在 盐酸 、 氢碘酸 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 79.08h， 生成 (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 3,5-acetonide
  参考文献：
  名称：

  Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide

  摘要：

  DOI：

  10.1016/s0040-4020(01)85115-2

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.
• PATERSON, IAN;ARYA, PRABHAT, TETRAHEDRON, 44,(1988) N 1, 253-260
  作者：PATERSON, IAN、ARYA, PRABHAT

  DOI：——

  日期：——