<3aR-(3aα,4α,5β,6β,6aα)>-5,6-Bis(benzyloxy)hexahydro-4-(1,1'-dimethoxymethyl)-2H-cyclopentafuran-2-one | 120927-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <3aR-(3aα,4α,5β,6β,6aα)>-5,6-Bis(benzyloxy)hexahydro-4-(1,1'-dimethoxymethyl)-2H-cyclopentafuran-2-one
• 英文别名: (3aR-(3aα,4α,5β,6β,6aα))-5,6-Bis(benzyloxy)hexahydro-4-(1,1'-dimethoxymethyl)-2H-cyclopenta[b]furan-2-one；(3aR,4S,5R,6S,6aR)-4-(dimethoxymethyl)-5,6-bis(phenylmethoxy)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 120927-65-3
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: UBXIUOLGJWHORW-OOWPADAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-葡萄烯糖 在 咪唑 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 三正丁基氢锡 、 四丁基碘化铵 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 20.25h， 生成 <3aR-(3aα,4α,5β,6β,6aα)>-5,6-Bis(benzyloxy)hexahydro-4-(1,1'-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

文献信息

• Intramolecular radical cyclizations of 2-deoxy-2-iodohexopyranoside derivatives: routes to densely functionalized carbocycles
  作者：Gregory D. Vite、Ricardo Alonso、Bert Fraser-Reid

  DOI：10.1021/jo00271a005

  日期：1989.5
• Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes
  作者：R. A. Alonso、G. D. Vite、R. E. McDevitt、B. Fraser-Reid

  DOI：10.1021/jo00028a033

  日期：1992.1

  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.