(3R,4S,5R,6S,7S,10R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one | 119887-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5R,6S,7S,10R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one
• CAS: 119887-68-2
• 化学式: C₃₅H₆₃NO₁₁
• 分子量: 673.885
• InChiKey: WHKOVLXQMZDBAS-LWIKJQIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S,7S,10R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one 在 盐酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 (2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5,9,11-tetrahydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide
  参考文献：
  名称：

  通过完整的糖苷配基油酸内酯合成油酸霉素

  摘要：

  通过将两个糖单元引入完整的糖苷配基油酸内酯中，重新构建了奥林霉素，该糖苷酸首先通过8-外-亚甲基衍生物的立体选择性氧化合成。

  DOI：

  10.1016/s0040-4039(00)80397-4
• 作为产物：
  描述：

  竹桃霉素 在 chromium dichloride 、 盐酸 、 sodium tetrahydroborate 作用下， 生成 (3R,4S,5R,6S,7S,10R,11R,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10,12-dihydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,11,13,14-hexamethyl-9-methylidene-oxacyclotetradecan-2-one
  参考文献：
  名称：

  通过完整的糖苷配基油酸内酯合成油酸霉素

  摘要：

  通过将两个糖单元引入完整的糖苷配基油酸内酯中，重新构建了奥林霉素，该糖苷酸首先通过8-外-亚甲基衍生物的立体选择性氧化合成。

  DOI：

  10.1016/s0040-4039(00)80397-4

文献信息

• Impact of stereochemistry on the biological activity of novel oleandomycin derivatives
  作者：Jurica Bauer、Mark Vine、Ilija Čorić、Martina Bosnar、Ivanka Pašalić、Gordana Turkalj、Gorjana Lazarevski、Ognjen Čulić、Goran Kragol

  DOI：10.1016/j.bmc.2012.02.013

  日期：2012.4

  A set of 8-methylene-, 8-methyl-, and 8-methyl-9-dihydro-oleandomycin derivatives having different combinations of stereochemistries at positions C-8 and/or C-9 have been prepared in a chemoselective and stereoselective manner and tested in vitro for antibacterial activity and inhibition of IL-6 production. Configurations of the stereocenters at C-8 and C-9 were determined using 2D NMR techniques. We have shown that change of stereochemistry at these positions can exert a major influence on antibacterial activity as well as IL-6 inhibition, providing novel macrolide derivatives with diminished antibacterial and potent anti-inflammatory activity. In addition, the anti-inflammatory activity observed in vitro was confirmed in an in vivo model of lipopolysaccharide-induced inflammation. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of oleandomycin through the intact aglycone, oleandolide
  作者：Kuniaki Tatsuta、Yoshiyuki Kobayashi、Hiroki Gunji、Hirokazu Masuda

  DOI：10.1016/s0040-4039(00)80397-4

  日期：——

  Oleandomycin has been reconstructed by an introduction of the two sugar units onto the intact aglycone, oleandolide, which was first synthesized through the stereoselective oxidation of the 8-exo-methylene derivative.

  通过将两个糖单元引入完整的糖苷配基油酸内酯中，重新构建了奥林霉素，该糖苷酸首先通过8-外-亚甲基衍生物的立体选择性氧化合成。