2,3-O-Isopropyliden-D-lyxose-diethyl-dithioacetal | 159144-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-Isopropyliden-D-lyxose-diethyl-dithioacetal
• 英文别名: (1R)-1-[(4S,5S)-5-[bis(ethylsulfanyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 159144-39-5
• 化学式: C₁₂H₂₄O₄S₂
• 分子量: 296.452
• InChiKey: LPWNOTKGDBWAQD-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-O-Isopropyliden-D-lyxose-diethyl-dithioacetal 在 镍 lead(IV) acetate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.25h， 生成 4(R),5(R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638
• 作为产物：
  描述：

  (2R,3S,4S)-5,5-bis(ethylthio)pentane-1,2,3,4-tetraol 在 phosphorus pentoxide 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 3.25h， 生成 2,3-O-Isopropyliden-D-lyxose-diethyl-dithioacetal
  参考文献：
  名称：

  Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde

  摘要：

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

  DOI：

  10.1007/bf01277638

文献信息

• Eine einfache Synthese aller vier stereoisomeren 2,2,5-Trimethyl-1,3-dioxolan-4-carbaldehyde
  作者：W. H. Binder、R. H. Prenner、W. Schmid

  DOI：10.1007/bf01277638

  日期：1994.6

  A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.