[(3aR,4S,7aS)-7a-formyl-3a-methyl-4-[(2-methylpropan-2-yl)oxy]-2,3,4,5,6,7-hexahydro-1-benzofuran-2-yl] formate | 215371-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: [(3aR,4S,7aS)-7a-formyl-3a-methyl-4-[(2-methylpropan-2-yl)oxy]-2,3,4,5,6,7-hexahydro-1-benzofuran-2-yl] formate
• CAS: 215371-42-9
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: KRYICNNNVTVAIX-HAOUFUCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3aR,4S,7aS)-7a-formyl-3a-methyl-4-[(2-methylpropan-2-yl)oxy]-2,3,4,5,6,7-hexahydro-1-benzofuran-2-yl] formate 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 (1S,2R,3S)-2-(2-hydroxyethyl)-1-(hydroxymethyl)-2-methyl-3-[(2-methylpropan-2-yl)oxy]cyclohexan-1-ol
  参考文献：
  名称：

  A convenient preparation of taxoid right-half building blocks

  摘要：

  Wieland-Miescher ketone derived unsaturated diols 4 reacted with Pb(OAc)(4) to furnish tricyclic enolether intermediate 6 which upon ozonolysis gave access to useful synthetic intermediates such as bicyclic lactone 7, methyl furanoside 8 and triol 9 (taxoid right-half precursors), depending on the solvent used during the ozonolysis and the nature of the following synthetic operation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00289-4
• 作为产物：
  描述：

  (1R,5S,6R,8R)-6-methyl-5-[(2-methylpropan-2-yl)oxy]-9,12-dioxatricyclo[6.3.1.01,6]dodec-10-ene 在 臭氧 、 三苯基膦 作用下， 生成 [(3aR,4S,7aS)-7a-formyl-3a-methyl-4-[(2-methylpropan-2-yl)oxy]-2,3,4,5,6,7-hexahydro-1-benzofuran-2-yl] formate
  参考文献：
  名称：

  研究类紫杉醇的全合成。选定的不饱和双环二醇的四乙酸铅氧化

  摘要：

  描述了使用Wieland-Miescher酮衍生的二醇6和Hajos-Parrish酮衍生的二醇14的四乙酸铅裂解来合成紫杉烷骨架1的潜在的C-1 / C-15和C-2 / C-10亚基。

  DOI：

  10.1016/0040-4039(94)88172-3

文献信息

• Studies towards the total synthesis of taxoids. Lead tetraacetate oxidations of selected unsaturated bicyclic diols
  作者：S. Arseniyadis、D.V. Yashunsky、R. Brondi Alves、Q. Wang、E. Toromanoff、L. Toupet、P. Potier

  DOI：10.1016/0040-4039(94)88172-3

  日期：1994.1

  Syntheses of potential C-1/C-15 and C-2/C-10 subunits of taxoid skeleton 1 using lead tetraacetate cleavage of the Wieland-Miescher ketone derived diol 6 and the Hajos-Parrish ketone derived diol 14 are described.

  描述了使用Wieland-Miescher酮衍生的二醇6和Hajos-Parrish酮衍生的二醇14的四乙酸铅裂解来合成紫杉烷骨架1的潜在的C-1 / C-15和C-2 / C-10亚基。
• A convenient preparation of taxoid right-half building blocks
  作者：Siméon Arseniyadis、José Quilez del Moral、Rosemeire Brondi Alves、Pierre Potier、Loı̈c Toupet

  DOI：10.1016/s0957-4166(98)00289-4

  日期：1998.8

  Wieland-Miescher ketone derived unsaturated diols 4 reacted with Pb(OAc)(4) to furnish tricyclic enolether intermediate 6 which upon ozonolysis gave access to useful synthetic intermediates such as bicyclic lactone 7, methyl furanoside 8 and triol 9 (taxoid right-half precursors), depending on the solvent used during the ozonolysis and the nature of the following synthetic operation. (C) 1998 Elsevier Science Ltd. All rights reserved.