(2S,3S,4R,5S,6S,10S,11R)-5,11-dimethoxy-2,4,6,10-tetramethyltridecane-1,3,9,13-tetraol | 434284-35-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S,4R,5S,6S,10S,11R)-5,11-dimethoxy-2,4,6,10-tetramethyltridecane-1,3,9,13-tetraol
• 英文别名: (2S,3S,4R,5S,6S,10S,11R)-5,11-dimethoxy-2,4,6,10-tetramethyltridecane-1,3,9,13-tetrol
• CAS: 434284-35-2
• 化学式: C₁₉H₄₀O₆
• 分子量: 364.523
• InChiKey: AILIUALEACICNQ-QNIVFUQESA-N

物化性质

• 沸点：
  509.2±50.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (2S,3S,4R,5S,6S,10S,11R)-5,11-dimethoxy-2,4,6,10-tetramethyltridecane-1,3,9,13-tetraol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,3S,4R,5S,6S,10S,11R)-3,9-dihydroxy-5,11-dimethoxy-2,4,6,10-tetramethyl-13-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-tridecyl ester
  参考文献：
  名称：

  Stereochemical assignment of the C23–C35 portion of sphinxolide/reidispongiolide class of natural products by asymmetric synthesis

  摘要：

  The absolute configuration of the seven stereogenic centers contained in the C23-C35 portion of reidispongiolide A is determined by asymmetric synthesis of the corresponding fragment obtained by ozonolysis of the natural macrolide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00372-0
• 作为产物：
  描述：

  (3S,4S,5S,6S,7S)-6-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-3,5,7-trimethyl-1-octen-4-ol 在 platinum on activated charcoal 盐酸 、 barium dihydroxide 、 sodium tetrahydroborate 、 四氧化锇 、 N-甲基吲哚酮 、 2,6-二叔丁基吡啶 、 水 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 31.5h， 生成 (2S,3S,4R,5S,6S,10S,11R)-5,11-dimethoxy-2,4,6,10-tetramethyltridecane-1,3,9,13-tetraol
  参考文献：
  名称：

  Stereochemical assignment of the C23–C35 portion of sphinxolide/reidispongiolide class of natural products by asymmetric synthesis

  摘要：

  The absolute configuration of the seven stereogenic centers contained in the C23-C35 portion of reidispongiolide A is determined by asymmetric synthesis of the corresponding fragment obtained by ozonolysis of the natural macrolide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00372-0

文献信息

• Toward the Synthesis of Reidispongiolide A:  Stereocontrolled Synthesis of the C₁₇−C₂₂ and C₂₃−C₃₅ Degradation Fragments
  作者：Ian Paterson、Kate Ashton、Robert Britton、Henner Knust

  DOI：10.1021/ol034558y

  日期：2003.5.1

  reactions of chiral ketones, a highly stereocontrolled synthesis of each of the C(17)-C(22) and C(23)-C(35) degradation fragments of reidispongiolide A has been achieved. This permits a configurational assignment of the complete C(17)-C(36) region of this antimitotic macrolide, along with providing advanced intermediates for a projected total synthesis.

  [结构：见正文]依靠手性酮的不对称醛醇缩合反应，赖皮松内酯A的C（17）-C（22）和C（23）-C（35）降解片段均具有高度立体控制的合成实现了。这允许该抗有丝分裂大环内酯的完整C（17）-C（36）区域的配置分配，以及为计划的总合成提供高级中间体。
• Stereochemistry of Sphinxolides and Reidispongiolides. Asymmetric Synthesis of the C17−C22 Fragment of Reidispongiolide A
  作者：Angela Zampella、Carla Bassarello、Giuseppe Bifulco、Luigi Gomez-Paloma、Maria Valeria D'Auria

  DOI：10.1002/1099-0690(200203)2002:5<785::aid-ejoc785>3.0.co;2-n

  日期：2002.3
• Stereochemical assignment of the C23–C35 portion of sphinxolide/reidispongiolide class of natural products by asymmetric synthesis
  作者：Angela Zampella、Valentina Sepe、Rosa D'Orsi、Giuseppe Bifulco、Carla Bassarello、Maria Valeria D'Auria

  DOI：10.1016/s0957-4166(03)00372-0

  日期：2003.7

  The absolute configuration of the seven stereogenic centers contained in the C23-C35 portion of reidispongiolide A is determined by asymmetric synthesis of the corresponding fragment obtained by ozonolysis of the natural macrolide. (C) 2003 Elsevier Science Ltd. All rights reserved.