(2R,3S,4R,5R,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethyl-5,7-bis(triethylsilyloxy)undec-8-enal | 1187629-54-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3S,4R,5R,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethyl-5,7-bis(triethylsilyloxy)undec-8-enal
• 英文别名: (E,2R,3S,4R,5R,6S,7R)-11-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-2,4,6,8-tetramethyl-5,7-bis(triethylsilyloxy)undec-8-enal
• CAS: 1187629-54-4
• 化学式: C₄₄H₇₆O₅Si₃
• 分子量: 769.341
• InChiKey: CZYPNBBHVBYOFX-IDURVUMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-(trimethylsilyl)ethyl 6-(diethoxyphosphoryl)hexa-2,4-dienoate 、 (2R,3S,4R,5R,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethyl-5,7-bis(triethylsilyloxy)undec-8-enal 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以330 mg的产率得到(2E,4E,6E,8S,9R,10R,11R,12S,13R,14E)-2-(trimethylsilyl)ethyl 17-(tert-butyldiphenylsilyloxy)-9-methoxy-8,10,12,14-tetramethyl-11,13-bis(triethylsilyloxy)heptadeca-2,4,6,14-tetraenoate
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833
• 作为产物：
  描述：

  (9R,10S,11R,12R,13R,14S,E)-17,17-diethyl-13-methoxy-2,2,8,10,12,14-hexamethyl-3,3-diphenyl-9,11-bis(triethylsilyloxy)-4,16-dioxa-3,17-disilanonadec-7-ene 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4R,5R,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethyl-5,7-bis(triethylsilyloxy)undec-8-enal
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833

文献信息

• Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide
  作者：Etienne Fleury、Marie-Isabelle Lannou、Olivia Bistri、François Sautel、Georges Massiot、Ange Pancrazi、Janick Ardisson

  DOI：10.1021/jo9012833

  日期：2009.9.18

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.