(R)-3-acetoxy-2-hydroxymethylpropanal diethyl acetal | 188761-13-9

• 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: (R)-3-acetoxy-2-hydroxymethylpropanal diethyl acetal
• 英文别名: [(2R)-3,3-diethoxy-2-(hydroxymethyl)propyl] acetate
• CAS: 188761-13-9
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: TUOCVKSJGLGDRU-SECBINFHSA-N

物化性质

• 沸点：
  305.1±42.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-acetoxy-2-hydroxymethylpropanal diethyl acetal 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-[(2R)-3,3-diethoxy-2-(hydroxymethyl)propyl]formamide
  参考文献：
  名称：

  Homoisofagomines: Chemical-enzymatic synthesis and evaluation as α- and β-glucosidase inhibitors

  摘要：

  Methyl- and hydroxymethyl derivatives of the highly potent glycosidase inhibitor isofagomine are accessible via aldolase-catalyzed C-C bond formation and competitively inhibit beta-glucosidase at low micromolar concentrations. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00042-6
• 作为产物：
  描述：

  乙酸乙烯酯 、 1,1-diethoxy-3-hydroxy-2-(hydroxymethyl)propane 在 lipase from Pseudomonas fluorescens 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 10.0h， 生成 (R)-3-acetoxy-2-hydroxymethylpropanal diethyl acetal 、 (S)-3-acetoxy-2-hydroxymethylpropanal diethyl acetal
  参考文献：
  名称：

  Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals

  摘要：

  Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PfL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00018-9