1-[(4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethanone | 137553-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethanone
• CAS: 137553-92-5
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: MDUGUCCXNCAQHS-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1-[(4R,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7
• 作为产物：
  描述：

  O¹-phosphono-D-threo-5,6-dideoxy-[2]hexulose 在 zinc(II) iodide 作用下， 生成 1-[(4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethanone
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7

文献信息

• A transketolase-based synthesis of (+)-exo-brevicomin
  作者：David C. Myles、Peter J. Andrulis、George M. Whitesides

  DOI：10.1016/s0040-4039(00)93473-7

  日期：1991.9

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.