[(1R,2E,4E,6R,8E)-1-[(2R,4R,6S)-4,6-dimethoxy-6-[(4-trimethylstannyl-1,3-oxazol-2-yl)methyl]oxan-2-yl]-6-methoxy-3-methyl-9-trimethylsilylnona-2,4,8-trienoxy]-tri(propan-2-yl)silane | 1010440-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [(1R,2E,4E,6R,8E)-1-[(2R,4R,6S)-4,6-dimethoxy-6-[(4-trimethylstannyl-1,3-oxazol-2-yl)methyl]oxan-2-yl]-6-methoxy-3-methyl-9-trimethylsilylnona-2,4,8-trienoxy]-tri(propan-2-yl)silane
• CAS: 1010440-88-6
• 化学式: C₃₇H₆₉NO₆Si₂Sn
• 分子量: 798.839
• InChiKey: SHJZQARMOSEJSH-KVBNMQAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,6E,9R,11R,12R,13S,16Z,19S,23R,25R,27R,31S)-27-[tert-butyl(dimethyl)silyl]oxy-11-[(E)-1-iodoprop-1-en-2-yl]-12,31-dimethyl-21-methylidene-4,10,14,29,30-pentaoxa-32-azapentacyclo[23.3.1.12,5.19,13.119,23]dotriaconta-2,5(32),6,16-tetraen-15-one 、 [(1R,2E,4E,6R,8E)-1-[(2R,4R,6S)-4,6-dimethoxy-6-[(4-trimethylstannyl-1,3-oxazol-2-yl)methyl]oxan-2-yl]-6-methoxy-3-methyl-9-trimethylsilylnona-2,4,8-trienoxy]-tri(propan-2-yl)silane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三苯胂 、 N,N-二异丙基乙胺 、 Tetrabutylammoniumsalz der Diphenylphosphinsaeure 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以76%的产率得到
  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.