(2S,3R,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide | 1187629-48-6

• 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: (2S,3R,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide
• 英文别名: (2S,3R,4R,5R,6S)-7-[tert-butyl(dimethyl)silyl]oxy-N,5-dimethoxy-N,2,4,6-tetramethyl-3-trimethylsilyloxyheptanamide
• CAS: 1187629-48-6
• 化学式: C₂₂H₄₉NO₅Si₂
• 分子量: 463.806
• InChiKey: NTOMFTKTRKGFPO-PXTPFGJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide 在 叔丁基锂 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 1.17h， 生成 (4S,5R,6R,7R,8S,E)-9-(tert-butyldimethylsilyloxy)-5-hydroxy-7-methoxy-2,4,6,8-tetramethyl-1-(trimethylsilyl)non-1-en-3-one
  参考文献：
  名称：

  杀虫剂的综合研究：趋向于C1-C25片段的融合方法的发展

  摘要：

  hemicalide的合成研究是一种最近分离的海洋天然产物，显示出强大的抗增殖活性和独特的作用方式，强调了可靠的Horner-Wadsworth-Emmons烯烃聚合反应可生成C6-C7烯烃，并形成了有效的Suzuki-Miyaura偶联反应C15–C16键，导致针对C1–C25片段的收敛方法的发展。

  DOI：

  10.1021/ol402077e
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 (2S,3R,4S,5R,6S)-7-(tert-butyldimethylsilyloxy)-3-hydroxy-N,5-dimethoxy-N,2,4,6-tetramethylheptanamide 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(2S,3R,4R,5R,6S)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide
  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.
• Synthetic Studies on Hemicalide: Development of a Convergent Approach toward the C1–C25 Fragment
  作者：Geoffroy Sorin、Etienne Fleury、Christine Tran、Elise Prost、Nicolas Molinier、François Sautel、Georges Massiot、Simon Specklin、Christophe Meyer、Janine Cossy、Marie-Isabelle Lannou、Janick Ardisson

  DOI：10.1021/ol402077e

  日期：2013.9.20

  Synthetic studies on hemicalide, a recently isolated marine natural product displaying highly potent antiproliferative activity and a unique mode of action, have highlighted a reliable Horner–Wadsworth–Emmons olefination to create the C6–C7 alkene and a remarkable efficient Suzuki–Miyaura coupling to form the C15–C16 bond, resulting in the development of a convergent approach toward the C1–C25 fragment

  hemicalide的合成研究是一种最近分离的海洋天然产物，显示出强大的抗增殖活性和独特的作用方式，强调了可靠的Horner-Wadsworth-Emmons烯烃聚合反应可生成C6-C7烯烃，并形成了有效的Suzuki-Miyaura偶联反应C15–C16键，导致针对C1–C25片段的收敛方法的发展。