(2S,3R,4R,5R,6R)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide | 1187629-95-3

• 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,6R)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide
• 英文别名: (2S,3R,4R,5R,6R)-7-[tert-butyl(dimethyl)silyl]oxy-N,5-dimethoxy-N,2,4,6-tetramethyl-3-trimethylsilyloxyheptanamide
• CAS: 1187629-95-3
• 化学式: C₂₂H₄₉NO₅Si₂
• 分子量: 463.806
• InChiKey: NTOMFTKTRKGFPO-OUUBHVDSSA-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：

  (E)-(4-bromopent-3-enyloxy)(tert-butyl)diphenylsilane 、 (2S,3R,4R,5R,6R)-7-(tert-butyldimethylsilyloxy)-N,5-dimethoxy-N,2,4,6-tetramethyl-3-(trimethylsilyloxy)heptanamide 在 叔丁基锂 、 amberlyst-15 作用下， 以 乙醚 、 正戊烷 、 甲醇 为溶剂， 反应 1.5h， 以78%的产率得到(10S,11R,12S,13R,14R,E)-11-hydroxy-13-methoxy-2,2,8,10,12,14,17,17,18,18-decamethyl-3,3-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one
  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：

  三氟甲磺酸三甲基硅酯 、 (2S,3R,4S,5R,6R)-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,6R)-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.