(3S)-3,4-dibenzyloxy-3-methyl-butan-2-one | 1366453-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-3,4-dibenzyloxy-3-methyl-butan-2-one
• 英文别名: (3S)-3-methyl-3,4-bis(phenylmethoxy)butan-2-one
• CAS: 1366453-82-8
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: GQYDFQUUWAWALD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  (3S)-3,4-dibenzyloxy-3-methyl-butan-2-one 、 环丙甲醛 在 氯代二环己基硼烷 、 三乙胺 、 双氧水 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 1.5h， 生成 (1S,4S)-1-cyclopropyl-1-hydroxy-4-methyl-4,5-bis(phenylmethoxy)pentan-3-one 、 (1R,4S)-4,5-bis(benzyloxy)-1-cyclopropyl-1-hydroxy-4-methylpentan-3-one
  参考文献：
  名称：

  1,4-Induction in aldol reactions of (tertiary α′-alkoxy)methyl ketones: synthesis of the C8–C11 stereotriad of ent-fostriecin

  摘要：

  A diastereoselective, boron-mediated aldol process inspired by the natural product fostriecin is described. Using a tertiary alpha'-stereocenter as the induction element, aldol adducts are provided with high yields, good to excellent levels of diastereoselection, and broad substrate scope. An Evans-Tischencko reduction of the aldol adduct from cinnamaldehyde resulted in the C-8-C-11 stereotriad of ent-fostriecin. 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.130
• 作为产物：
  描述：

  (S)-N,2,3-tris(benzyloxy)-N,2-dimethylpropanamide 、 甲基锂 以 乙醚 为溶剂， 以58%的产率得到(3S)-3,4-dibenzyloxy-3-methyl-butan-2-one
  参考文献：
  名称：

  1,4-Induction in aldol reactions of (tertiary α′-alkoxy)methyl ketones: synthesis of the C8–C11 stereotriad of ent-fostriecin

  摘要：

  A diastereoselective, boron-mediated aldol process inspired by the natural product fostriecin is described. Using a tertiary alpha'-stereocenter as the induction element, aldol adducts are provided with high yields, good to excellent levels of diastereoselection, and broad substrate scope. An Evans-Tischencko reduction of the aldol adduct from cinnamaldehyde resulted in the C-8-C-11 stereotriad of ent-fostriecin. 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.130

文献信息

• 1,4-Induction in aldol reactions of (tertiary α′-alkoxy)methyl ketones: synthesis of the C8–C11 stereotriad of ent-fostriecin
  作者：Nicholas Cowper、Soula Azzi、Kristina Dupont-Gaudet、Jason D. Burch

  DOI：10.1016/j.tetlet.2012.01.130

  日期：2012.4

  A diastereoselective, boron-mediated aldol process inspired by the natural product fostriecin is described. Using a tertiary alpha'-stereocenter as the induction element, aldol adducts are provided with high yields, good to excellent levels of diastereoselection, and broad substrate scope. An Evans-Tischencko reduction of the aldol adduct from cinnamaldehyde resulted in the C-8-C-11 stereotriad of ent-fostriecin. 2012 Elsevier Ltd. All rights reserved.