(2S,3aS,4R,5R,7aS)-7-bromo-4,5-bis(methoxymethoxy)-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole | 1035055-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3aS,4R,5R,7aS)-7-bromo-4,5-bis(methoxymethoxy)-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole
• CAS: 1035055-71-0
• 化学式: C₁₈H₂₃BrO₇
• 分子量: 431.28
• InChiKey: KNFJOUPNGWANHC-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3aS,4R,5R,7aS)-7-bromo-4,5-bis(methoxymethoxy)-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole 在 二异丁基氢化铝 作用下， 以84%的产率得到(1S,2S,5R,6S)-2-(4-methoxybenzyloxy)-3-bromo-5,6-bis(methoxymethoxy)cyclohex-3-enol
  参考文献：
  名称：

  A chemoenzymatic total synthesis of ent-narciclasine

  摘要：

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.113
• 作为产物：
  描述：

  (2S,3aS,4R,5R,7aS)-7-bromo-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol 、 氯甲基甲基醚 以75%的产率得到(2S,3aS,4R,5R,7aS)-7-bromo-4,5-bis(methoxymethoxy)-2-(4-methoxyphenyl)-3a,4,5,7a-tetrahydro-1,3-benzodioxole
  参考文献：
  名称：

  A chemoenzymatic total synthesis of ent-narciclasine

  摘要：

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.113

文献信息

• A chemoenzymatic total synthesis of ent-narciclasine
  作者：Maria Matveenko、Martin G. Banwell、Anthony C. Willis

  DOI：10.1016/j.tet.2008.01.113

  日期：2008.5

  The synthesis of the title compound [(-)-1] has been achieved, for the first time, by reacting the aryl boronic acid ester 4 with the amino-conduritol derivative 6 under Suzuki-Miyaura cross-coupling conditions then subjecting the product phenanthridinone 23 to a global deprotection process using trimethylsilyl bromide. The aromatic building block 4 was prepared in ten steps from piperonal while compound 6 was obtained in nine steps from the enantiomerically pure cis-1,2-dihydrocatechol 7. This last compound is available, in multi-gram quantities, through a whole-cell-mediated biotransformation of bromobenzene using genetically engineered organisms that over-express the responsible enzyme, namely toluene dioxygenase. Since the enantiomer of compound 7 is available by related means, the present work also represents a formal total synthesis of the alkaloid narciclasine [(+)-1]. The single-crystal X-ray analysis of compound 13 is reported. (C) 2008 Elsevier Ltd. All rights reserved.