[(2S)-1-methoxy-1-oxopropan-2-yl] 2-oxopyran-3-carboxylate | 145364-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [(2S)-1-methoxy-1-oxopropan-2-yl] 2-oxopyran-3-carboxylate
• CAS: 145364-55-2
• 化学式: C₁₀H₁₀O₆
• 分子量: 226.186
• InChiKey: GDRYNXFXCCLBEW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-1-methoxy-1-oxopropan-2-yl] 2-oxopyran-3-carboxylate 在 双(乙腈)氯化钯(II) N-甲基吗啉 、 (-)-Pr(hfc)3 作用下， 以 乙醚 、 乙醇 、 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， -30.0~25.0 ℃ 、1200.0 MPa 条件下， 反应 240.67h， 生成 (4R,6S)-4,6-Dihydroxy-cyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  A new and efficient asymmetric synthesis of an A-ring precursor to physiologically active 1.alpha.-hydroxyvitamin D3 steroids

  摘要：

  A highly stereocontrolled and mild Diels-Alder cycloaddition involving stereochemically matched pyrone (S)-lactate 4 and Lewis acid (-)-Pr(hfc)3 produced bicyclic lactone endo-5 via a double stereodifferentiation process. Bicyclic lactone 5 was then transformed smoothly and in high yield into phosphine oxide (-)-1, an important A-ring precursor to various physiologically active 1alpha-hydroxyvitamin D3 steroids.

  DOI：

  10.1021/jo00052a007
• 作为产物：
  描述：

  2-pyrone-3-carboxylic acid 在 草酰氯 作用下， 生成 [(2S)-1-methoxy-1-oxopropan-2-yl] 2-oxopyran-3-carboxylate
  参考文献：
  名称：

  A new and efficient asymmetric synthesis of an A-ring precursor to physiologically active 1.alpha.-hydroxyvitamin D3 steroids

  摘要：

  A highly stereocontrolled and mild Diels-Alder cycloaddition involving stereochemically matched pyrone (S)-lactate 4 and Lewis acid (-)-Pr(hfc)3 produced bicyclic lactone endo-5 via a double stereodifferentiation process. Bicyclic lactone 5 was then transformed smoothly and in high yield into phosphine oxide (-)-1, an important A-ring precursor to various physiologically active 1alpha-hydroxyvitamin D3 steroids.

  DOI：

  10.1021/jo00052a007

文献信息

• Posner Gary H., Carry Jean-Christophe, Lee Jae Kyoo, Bull D. Scott, Dai H+, Tetrahedron Lett, 35 (1994) N 9, S 1321-1324
  作者：Posner Gary H., Carry Jean-Christophe, Lee Jae Kyoo, Bull D. Scott, Dai H+

  DOI：——

  日期：——
• A new and efficient asymmetric synthesis of an A-ring precursor to physiologically active 1.alpha.-hydroxyvitamin D3 steroids
  作者：Gary H. Posner、Jean Christophe Carry、Tizah E. N. Anjeh、Andrew N. French

  DOI：10.1021/jo00052a007

  日期：1992.12

  A highly stereocontrolled and mild Diels-Alder cycloaddition involving stereochemically matched pyrone (S)-lactate 4 and Lewis acid (-)-Pr(hfc)3 produced bicyclic lactone endo-5 via a double stereodifferentiation process. Bicyclic lactone 5 was then transformed smoothly and in high yield into phosphine oxide (-)-1, an important A-ring precursor to various physiologically active 1alpha-hydroxyvitamin D3 steroids.