(2R,3R,5S,6R)-2,3-bis-(tert-butyl-dimethyl-silyloxy)-5-((1E,3E)-hepta-1,3-dienyl)-4-hydroxymethyl-cyclohexanone | 1166841-84-4

• 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,5S,6R)-2,3-bis-(tert-butyl-dimethyl-silyloxy)-5-((1E,3E)-hepta-1,3-dienyl)-4-hydroxymethyl-cyclohexanone
• 英文别名: (2R,3R,5S,6R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[(1E,3E)-hepta-1,3-dienyl]-6-(hydroxymethyl)cyclohexan-1-one
• CAS: 1166841-84-4
• 化学式: C₂₆H₅₀O₄Si₂
• 分子量: 482.852
• InChiKey: DQOQPJFEGQKKHP-VCZOYHTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S,6R)-2,3-bis-(tert-butyl-dimethyl-silyloxy)-5-((1E,3E)-hepta-1,3-dienyl)-4-hydroxymethyl-cyclohexanone 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 以92%的产率得到徘徊青霉素
  参考文献：
  名称：

  Asymmetric synthesis of palitantin by an enzymatic and organocatalytic approach

  摘要：

  The natural enantiomer of the fungal metabolite (+)-palitantin has been synthesized by adopting a chemoenzymatic and organocatalytic approach. Lipase catalyzed kinetic resolution, Sharpless asymmetric dihydroxylation and organocatalytic asymmetric hydroxymethylation are the key steps involved in the total synthesis of the target molecule. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.055
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 、 (2R,3R,5R)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-((1E,3E)-hepta-1,3-dienyl)-cyclohexanone 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以50%的产率得到(2R,3R,5S,6R)-2,3-bis-(tert-butyl-dimethyl-silyloxy)-5-((1E,3E)-hepta-1,3-dienyl)-4-hydroxymethyl-cyclohexanone
  参考文献：
  名称：

  Asymmetric synthesis of palitantin by an enzymatic and organocatalytic approach

  摘要：

  The natural enantiomer of the fungal metabolite (+)-palitantin has been synthesized by adopting a chemoenzymatic and organocatalytic approach. Lipase catalyzed kinetic resolution, Sharpless asymmetric dihydroxylation and organocatalytic asymmetric hydroxymethylation are the key steps involved in the total synthesis of the target molecule. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.055

文献信息

• Asymmetric synthesis of palitantin by an enzymatic and organocatalytic approach
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2009.02.055

  日期：2009.3

  The natural enantiomer of the fungal metabolite (+)-palitantin has been synthesized by adopting a chemoenzymatic and organocatalytic approach. Lipase catalyzed kinetic resolution, Sharpless asymmetric dihydroxylation and organocatalytic asymmetric hydroxymethylation are the key steps involved in the total synthesis of the target molecule. (C) 2009 Elsevier Ltd. All rights reserved.