(3aR,4S,5R,6R,6aR)-4-Dimethoxymethyl-5,6-dihydroxy-hexahydro-cyclopenta[b]furan-2-one | 137792-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3aR,4S,5R,6R,6aR)-4-Dimethoxymethyl-5,6-dihydroxy-hexahydro-cyclopenta[b]furan-2-one
• CAS: 137792-94-0
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: VLOHOKCUBWTLOU-PMPOVCSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3aR,4S,5R,6R,6aR)-4-Dimethoxymethyl-5,6-dihydroxy-hexahydro-cyclopenta[b]furan-2-one 在 4-二甲氨基吡啶 作用下， 以 乙酸乙酯 为溶剂， 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
• 作为产物：
  描述：

  Ethyl 1,2,6,7-Tetradeoxy-3,4-isopropylidene-D-lyxo-octa-1,6(Z)-dieno-1,5-pyranosuronate 在 camphor-10-sulfonic acid N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 (3aR,4S,5R,6R,6aR)-4-Dimethoxymethyl-5,6-dihydroxy-hexahydro-cyclopenta[b]furan-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