(2S,3R,4S,5S,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethylundec-8-ene-1,5,7-triol | 1187629-60-2

• 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,4S,5S,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethylundec-8-ene-1,5,7-triol
• 英文别名: (E,2S,3R,4S,5S,6S,7R)-11-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-2,4,6,8-tetramethylundec-8-ene-1,5,7-triol
• CAS: 1187629-60-2
• 化学式: C₃₂H₅₀O₅Si
• 分子量: 542.832
• InChiKey: IFWKPAKPJUJESN-SOGNYUBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethylundec-8-ene-1,5,7-triol 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以99%的产率得到(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
  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,11S,12S,13R,14S,E)-13-methoxy-2,2,8,10,12,14,17,17,18,18-decamethyl-3,3-diphenyl-4,16-dioxa-3,17-disilanonadec-7-ene-9,11-diol 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以88%的产率得到(2S,3R,4S,5S,6S,7R,E)-11-(tert-butyldiphenylsilyloxy)-3-methoxy-2,4,6,8-tetramethylundec-8-ene-1,5,7-triol
  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.