3,4-O-isopropylidene-5-deoxy-D-lyxitol | 155012-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-O-isopropylidene-5-deoxy-D-lyxitol
• 英文别名: 5-Deoxy-3,4-O-isopropyliden-D-lyxitol；(1R)-1-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 155012-75-2
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: QIGIJTXKTYJENP-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-5-deoxy-D-lyxitol 在 lead(IV) acetate 、 indium 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.17h， 生成 (1S)-1-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]but-3-en-1-ol
  参考文献：
  名称：

  Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates

  摘要：

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

  DOI：

  10.1016/s0040-4020(01)80790-0
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-arabinose diethyl dithio acetal 在 镍 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到3,4-O-isopropylidene-5-deoxy-D-lyxitol
  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