[(2R,4R)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2,4-dimethyl-7-oxoheptyl] N-tert-butylcarbamate | 1283733-25-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,4R)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2,4-dimethyl-7-oxoheptyl] N-tert-butylcarbamate
• CAS: 1283733-25-4
• 化学式: C₂₄H₃₆N₂O₅
• 分子量: 432.56
• InChiKey: KWPBFLAMJBZRQU-GGPKGHCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R,4R)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2,4-dimethyl-7-oxoheptyl] N-tert-butylcarbamate 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以72%的产率得到[(2R,4S,6S)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2,4,6-trimethyl-7-oxoheptyl] N-tert-butylcarbamate
  参考文献：
  名称：

  A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone

  摘要：

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.

  DOI：

  10.1021/jo202330b
• 作为产物：
  描述：

  在 C₃₂H₁₂BF₂₄^(1-)*C₃₉H₅₀IrNOP⁽¹⁺⁾ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、9.0 MPa 条件下， 反应 18.0h， 生成 [(2R,4R)-7-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2,4-dimethyl-7-oxoheptyl] N-tert-butylcarbamate
  参考文献：
  名称：

  A General, Asymmetric, and Noniterative Synthesis of Trideoxypropionates. Straightforward Syntheses of the Pheromones (+)-Vittatalactone and (+)-Norvittatalactone

  摘要：

  A novel, highly stereocontrolled, and very flexible synthetic access to biologically relevant trideoxypropionate building blocks in optically pure form has been developed. On the basis of a three-step sequence comprising a thermal oxy-Cope rearrangement, an iridium-catalyzed hydrogenation, and an auxiliary-controlled enolate methylation, trideoxypropionates with easily adjustable relative configuration were synthesized in excellent yields. In addition, the functionalized end groups allow for chemoselective manipulations and further elongation of the chain. The underlying strategy constitutes the first noniterative process for the assembly of polydeoxypropionates and has further been applied in total syntheses of the pheromones (+)-vittatalactone and (+)-norvittatalactone, which had been isolated from the striped cucumber beetle Acalymma vittatum.

  DOI：

  10.1021/jo202330b

文献信息

• A non-iterative, flexible, and highly stereoselective synthesis of polydeoxypropionates—synthesis of (+)-vittatalactone
  作者：Christian F. Weise、Matthias Pischl、Andreas Pfaltz、Christoph Schneider

  DOI：10.1039/c0cc05215a

  日期：——

  A short sequence comprising an oxy-Cope rearrangement, iridium-catalyzed hydrogenation, and enolate methylation provides trideoxypropionates with excellent diastereocontrol. A straightforward synthesis of the cucumber beetle pheromone (+)-vittatalactone illustrates this new strategy.

  一个简短的反应序列，包括氧-科普重排、铱催化氢化和烯醇盐甲基化，提供了具有出色的非对映选择性的三脱氧丙酸酯。黄瓜甲虫信息素（+）-维塔酮的简单合成展示了这一新策略。