(8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide | 116417-70-0

• 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
• 英文别名: (3R,4S,5R,6S,7S,9S,11R,12S,13R,14R)-4,6,9,12-tetrahydroxy-9-(iodomethyl)-3,5,7,11,13,14-hexamethyl-oxacyclotetradecane-2,10-dione
• CAS: 116417-70-0
• 化学式: C₂₀H₃₅IO₇
• 分子量: 514.398
• InChiKey: ZSVWMSQZGJYYAG-HRVFELILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide 在 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 oleandonolide 3,5-acetonide
  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'-acetyl-3'-de(dimethylamino)-3',4'-dehydrooleandomycin 在 盐酸 、 氢碘酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 60.25h， 生成 (8S)-8,8a-deepoxy-8-hydroxy-8a-iodooleandonolide
  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

• Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis
  作者：Jia-Hui Tay、Alonso J. Argüelles、Matthew D. DeMars、Paul M. Zimmerman、David H. Sherman、Pavel Nagorny

  DOI：10.1021/jacs.7b03198

  日期：2017.6.28

  selective glycosylations at the C5 positions of macrolactones (up to 99:1 rr), whereas the use of SPINOL-based CPAs resulted in selectivity switch and glycosylation of the C3 alcohol (up to 91:9 rr). Additionally, the C11 position of macrolactones was selectively functionalized through traceless protection of the C3/C5 diol with boronic acids prior to glycosylation. Investigation of the reaction mechanism

  这项工作描述了使用手性催化剂控制复杂多元醇（如 6-脱氧赤藓糖苷 B 和夹竹桃霉素衍生的大环内酯）糖基化的位点选择性的第一个例子。通过选择合适的手性酸作为催化剂或通过引入基于化学计量的硼酸添加剂，可以在大环内酯的 C3、C5 和 C11 位置区域发散地引入糖。基于 BINOL 的手性磷酸 (CPA) 用于催化大环内酯 C5 位置的高选择性糖基化（高达 99:1 rr），而使用基于 SPINOL 的 CPA 导致 C3 醇的选择性转换和糖基化（高达 91:9 rr)。此外，通过在糖基化之前用硼酸对 C3/C5 二醇进行无痕保护，大环内酯的 C11 位置被选择性功能化。对 CPA 控制的糖基化反应机制的研究揭示了共价连接的异头磷酸酯的参与，而不是作为反应中间体的氧碳鎓离子对。
• 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.
• Deconstruction−Reconstruction Strategy for Accessing Valuable Polyketides. Preparation of the C15−C24 Stereopentad of Discodermolide
  作者：Kathlyn A. Parker、Peng Wang

  DOI：10.1021/ol702144u

  日期：2007.11.1

  An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks.
• PATERSON, IAN;ARYA, PRABHAT, TETRAHEDRON, 44,(1988) N 1, 253-260
  作者：PATERSON, IAN、ARYA, PRABHAT

  DOI：——

  日期：——