Acetic acid (3aR,5R,6R,6aR)-5-((S)-1-acetoxy-2-iodo-ethyl)-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester | 151426-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3aR,5R,6R,6aR)-5-((S)-1-acetoxy-2-iodo-ethyl)-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• 英文别名: [(1S)-1-[(3aR,5R,6R,6aR)-6-acetyloxy-6-ethynyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]-2-iodoethyl] acetate
• CAS: 151426-62-9
• 化学式: C₁₅H₁₉IO₇
• 分子量: 438.216
• InChiKey: ZNSUVJYPBQIVNU-ZHZXCYKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (3aR,5R,6R,6aR)-5-((S)-1-acetoxy-2-iodo-ethyl)-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 [(1R,2R,6R,8R,9R)-1-acetyloxy-4,4-dimethyl-11-methylidene-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-9-yl] acetate 、 Acetic acid (3aR,4aR,5R,8aR,8bR)-5-acetoxy-2,2-dimethyl-3a,5,6,8b-tetrahydro-4aH-benzo[4,5]furo[2,3-d][1,3]dioxol-8a-yl ester
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8
• 作为产物：
  描述：

  3-C-ethynyl-1,2:5,6-di-O-isopropylidene-D-glucofuranoside 在 吡啶 、 溶剂黄146 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 Acetic acid (3aR,5R,6R,6aR)-5-((S)-1-acetoxy-2-iodo-ethyl)-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8

文献信息

• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.