[(3aR,7R,7aR)-6-oxo-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate | 165876-63-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: [(3aR,7R,7aR)-6-oxo-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 165876-63-1
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: LRQODMKDSYMFRI-ZXRVKKJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四氯化碳 、 [(3aR,7R,7aR)-6-oxo-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以20%的产率得到2,6-anhydro-3-O-acetyl-1-deoxy-1,1-dichloro-4,5-O-benzylidene-D-ribo-hex-1-enitol
  参考文献：
  名称：

  Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane

  摘要：

  Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted gamma and delta-lactones and some esters to afford the corresponding dichloroolefins in good yields. This new Wittig-type reaction provides an easy entry to this new class of compounds and tolerates a large variety of protecting groups. Application of this methodology to the dichloroolefination of simple lactones, sugar-derived lactones, and other biologically significant lactones is described.

  DOI：

  10.1021/jo00098a039
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 盐酸 作用下， 反应 7.0h， 生成 [(3aR,7R,7aR)-6-oxo-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
  参考文献：
  名称：

  Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone

  摘要：

  Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-D-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl donors to either of the hydroxyl groups of ribitol and can be applied for the preparation of polyhydroxylated compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.008