(2R,3R,4S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2,4-dimethylpentanal | 1187629-50-0

• 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,3R,4S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2,4-dimethylpentanal
• 英文别名: (2R,3R,4S)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2,4-dimethylpentanal
• CAS: 1187629-50-0
• 化学式: C₁₄H₃₀O₃Si
• 分子量: 274.476
• InChiKey: JBXQXAJGVWBSIU-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2,4-dimethylpentanal 、 (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到(S)-4-benzyl-3-((2S,3R,4S,5R,6S)-7-(tert-butyldimethylsilyloxy)-3-hydroxy-5-methoxy-2,4,6-trimethylheptanoyl)oxazolidin-2-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：

  (2S,4S,5R,6S)-7-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-4,6-dimethylheptane-2,3-diol 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.42h， 以2 g的产率得到(2R,3R,4S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2,4-dimethylpentanal
  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.