(4S,5S)-5-[(E)-3-(2-formyl-3,5-dimethoxyphenyl)prop-2-enyl]-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide | 1216817-96-7

• 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: (4S,5S)-5-[(E)-3-(2-formyl-3,5-dimethoxyphenyl)prop-2-enyl]-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
• CAS: 1216817-96-7
• 化学式: C₂₀H₂₇NO₇
• 分子量: 393.437
• InChiKey: RJVHAVBNAFNKKC-RUEXWFJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-[(E)-3-(2-formyl-3,5-dimethoxyphenyl)prop-2-enyl]-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide 在 sodium chlorite 、 2-甲基-2-丁烯 、 sodium phosphate 作用下， 以 水 、 叔丁醇 为溶剂， 以75%的产率得到2,4-dimethoxy-6-[(E)-3-[(4S,5S)-5-[methoxy(methyl)carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-1-enyl]benzoic acid
  参考文献：
  名称：

  A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277

  摘要：

  The structure, 5, assigned to the resorcylic acid lactone L-783,290 has been prepared for the first time and in a modular fashion using a Heck reaction to link the readily available fragments 8 and 14. Chemoenzymatic methods were used to prepare the latter fragment, in enantiopure form, from chlorobenzene. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.067
• 作为产物：
  描述：

  (4S,5S)-N-methoxy-N,2,2-trimethyl-5-prop-2-enyl-1,3-dioxolane-4-carboxamide 、 2-iodo-4,6-dimethoxybenzaldehyde 在 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 、 (4S,5S)-5-[(E)-3-(2-formyl-3,5-dimethoxyphenyl)prop-2-enyl]-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277

  摘要：

  The structure, 5, assigned to the resorcylic acid lactone L-783,290 has been prepared for the first time and in a modular fashion using a Heck reaction to link the readily available fragments 8 and 14. Chemoenzymatic methods were used to prepare the latter fragment, in enantiopure form, from chlorobenzene. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.067

文献信息

• An Enantioselective Synthesis of the Resorcylic Acid Lactone L-783,277 via Addition of an Acetylide Anion to a Tethered Weinreb Amide
  作者：Martin G. Banwell、Andrew Lin、Anthony C. Willis

  DOI：10.3987/com-10-s(e)67

  日期：——

  Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78 degrees C.
• A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277
  作者：Andrew Lin、Anthony C. Willis、Martin G. Banwell

  DOI：10.1016/j.tetlet.2009.12.067

  日期：2010.2

  The structure, 5, assigned to the resorcylic acid lactone L-783,290 has been prepared for the first time and in a modular fashion using a Heck reaction to link the readily available fragments 8 and 14. Chemoenzymatic methods were used to prepare the latter fragment, in enantiopure form, from chlorobenzene. (C) 2009 Elsevier Ltd. All rights reserved.