(2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone | 936946-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-[(E,2S,3R,4S,5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2,4,6,8-tetramethyldec-8-enoyl]-1,3-oxazolidin-2-one
• CAS: 936946-38-2
• 化学式: C₃₀H₄₉NO₅Si
• 分子量: 531.808
• InChiKey: SWGRWXZXFIQLCT-MPJIEJESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone 在 4-甲基苯磺酸吡啶 、 氟化氢吡啶 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of the C23–C32 fragment of spirangien

  摘要：

  The synthesis of the C23-C32 fragment of spirangien A is reported using Evans' alkylation, Evans-Metternich aldol reaction and a substrate controlled stereoselective reduction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.081
• 作为产物：
  描述：

  (E)-2-methyl-2-buten-1-ol 在 吡啶 、 锂硼氢 、 tin(II) trifluoromethanesulfonate 、 zinc(II) tetrahydroborate 、 邻苯二甲酸二甲酯 、 sodium hexamethyldisilazane 、 三溴化磷 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 (2'S,3'R,4'S,5'S,6'S,8E,4S)-3-[(5-[tert-butyldimethylsilyloxy]-3-hydroxyl-2,4,6,8-tetramethyl-1-oxo-dec-8-enyl)-4-(phenylmethyl)]-2-oxazolidinone
  参考文献：
  名称：

  Synthesis of the C23–C32 fragment of spirangien

  摘要：

  The synthesis of the C23-C32 fragment of spirangien A is reported using Evans' alkylation, Evans-Metternich aldol reaction and a substrate controlled stereoselective reduction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.081

文献信息

• Stereoselective synthesis of the C13–32 spiroacetal fragment of spirangien A
  作者：Claire Gregg、Michael V. Perkins

  DOI：10.1016/j.tet.2013.06.012

  日期：2013.8

  Stereoselective synthesis of an advanced intermediate towards the highly cytotoxic polyketide metabolite spirangien A was achieved. A key step in the synthesis was installation of the C23 stereocentre by a substrate controlled C22-23 aldol reaction. Comparison of this result with previous literature reports suggests that the facial preference of the aldehyde controls the outcome of the C22-23 aldol coupling and depends on the 027/25 protecting groups when reacting with complex ketones, which contain the C17-15 stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.