(4R,6R)-4-methoxy-6-[(1R,2E,4E,6R,8Z)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-one | 1010440-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,6R)-4-methoxy-6-[(1R,2E,4E,6R,8Z)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-one
• CAS: 1010440-90-0
• 化学式: C₂₉H₅₄O₅Si₂
• 分子量: 538.916
• InChiKey: JZLIJGBGOZVYAP-KOLCDGIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4R,6R)-4-methoxy-6-[(1R,2E,4E,6R)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4-dien-8-ynyl]oxan-2-one 在 Lindlar's catalyst 喹啉 、 1-己烯 、 氢气 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 (4R,6R)-4-methoxy-6-[(1R,2E,4E,6R,8Z)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-one 、 (4R,6R)-4-methoxy-6-[(1R,2E,4E,6R,8E)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-one
  参考文献：
  名称：

  A Second-Generation Total Synthesis of (+)-Phorboxazole A

  摘要：

  A highly convergent second-generation synthesis of (+)-phorboxazole A has been achieved. Highlights of the synthetic approach include improved Petasis-Ferrier union/rearrangement conditions on a scale to assemble multigram quantities of the C(11-15) and C(22-26) cis-tetrahydropyrans inscribed with the phorboxazole architecture, a convenient method to prepare E- and Z-vinyl bromides from TMS-protected alkynes utilizing radical isomerization of Z-vinylsilanes, and a convergent late-stage Stille union to couple a fully elaborated C(1-28) macrocyclic iodide with a C(29-46) oxazole stannane side chain to establish the complete phorboxazole skeleton. The synthesis, achieved with a longest linear sequence of 24 steps, proceeded in 4.6% overall yield.

  DOI：

  10.1021/jo7018152

文献信息

• A Second-Generation Total Synthesis of (+)-Phorboxazole A
  作者：Amos B. Smith、Thomas M. Razler、Jeffrey P. Ciavarri、Tomoyasu Hirose、Tomoyasu Ishikawa、Regina M. Meis

  DOI：10.1021/jo7018152

  日期：2008.2.1

  A highly convergent second-generation synthesis of (+)-phorboxazole A has been achieved. Highlights of the synthetic approach include improved Petasis-Ferrier union/rearrangement conditions on a scale to assemble multigram quantities of the C(11-15) and C(22-26) cis-tetrahydropyrans inscribed with the phorboxazole architecture, a convenient method to prepare E- and Z-vinyl bromides from TMS-protected alkynes utilizing radical isomerization of Z-vinylsilanes, and a convergent late-stage Stille union to couple a fully elaborated C(1-28) macrocyclic iodide with a C(29-46) oxazole stannane side chain to establish the complete phorboxazole skeleton. The synthesis, achieved with a longest linear sequence of 24 steps, proceeded in 4.6% overall yield.