[2-[[(2S,4R,6R)-2,4-dimethoxy-6-[(1R,2E,4E,6R,8E)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-yl]methyl]-1,3-oxazol-4-yl] trifluoromethanesulfonate | 1010440-94-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [2-[[(2S,4R,6R)-2,4-dimethoxy-6-[(1R,2E,4E,6R,8E)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-yl]methyl]-1,3-oxazol-4-yl] trifluoromethanesulfonate
• CAS: 1010440-94-4
• 化学式: C₃₅H₆₀F₃NO₉SSi₂
• 分子量: 784.095
• InChiKey: SPGRSDOGBGFCMG-LPZGEPRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.88
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  甲醇 、 在 对甲苯磺酸 作用下， 反应 20.0h， 以0.74 mg的产率得到[2-[[(2S,4R,6R)-2,4-dimethoxy-6-[(1R,2E,4E,6R,8E)-6-methoxy-3-methyl-9-trimethylsilyl-1-tri(propan-2-yl)silyloxynona-2,4,8-trienyl]oxan-2-yl]methyl]-1,3-oxazol-4-yl] trifluoromethanesulfonate
  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.