3-C-allyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-ribo-furanose | 151426-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-C-allyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-ribo-furanose
• 英文别名: [(3aR,5R,6R,6aR)-6-hydroxy-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methyl methanesulfonate
• CAS: 151426-68-5
• 化学式: C₁₂H₂₀O₇S
• 分子量: 308.353
• InChiKey: YOSKTOIOKCAURV-DTHBNOIPSA-N

物化性质

• 沸点：
  453.3±40.0 °C(predicted)
• 密度：
  1.263±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-C-allyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-ribo-furanose 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.0h， 生成 (1R,2R,6R,8R,10S)-4,4,10-trimethyl-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-1-ol
  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：

  1-β-formyl-3-α-hydroxy-3-β-allyl-4α,5α-O-isopropylidene-tetrahydrofuran 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 3-C-allyl-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-ribo-furanose
  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.