<3aS-(4S,5R,6S,6aR)>-5,6-Diacetoxyhexahydro-4-(dimethoxymethyl)-2H-cyclopentafuran-2-one | 137792-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: <3aS-(4S,5R,6S,6aR)>-5,6-Diacetoxyhexahydro-4-(dimethoxymethyl)-2H-cyclopentafuran-2-one
• 英文别名: [(3aR,4S,5R,6S,6aR)-6-acetyloxy-4-(dimethoxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] acetate
• CAS: 137792-75-7
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: KQGVOSDOTFJEGE-GIVNFFOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3aR,4S,7aR)-2,2-Dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde 在 camphor-10-sulfonic acid 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 6.25h， 生成 <3aS-(4S,5R,6S,6aR)>-5,6-Diacetoxyhexahydro-4-(dimethoxymethyl)-2H-cyclopentafuran-2-one
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033