(1S,2R,6R,8R,11S)-4,4-dimethyl-N-phenylmethoxy-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-11-amine | 144733-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,6R,8R,11S)-4,4-dimethyl-N-phenylmethoxy-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-11-amine
• CAS: 144733-70-0
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: DNWCKYDYEGXZNS-ZVDSWSACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 5,6-dideoxy-1,2-O-isopropylidene-3-O-(S-methyl-thiocarbonate)-α-D-xylo-hepto-furanuronate 在 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.5h， 生成 (1S,2R,6R,8R,11S)-4,4-dimethyl-N-phenylmethoxy-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-11-amine
  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

• A new synthetic route to chiral, multiply functionalized cyclopentane rings
  作者：José Marco Contelles、Pilar Ruiz、Belén Sánchez、M.L. Jimeno

  DOI：10.1016/s0040-4039(00)79149-0

  日期：1992.9

  The tributyltin hydride mediated free radical cyclization of sugar derivatives 4–6 gives the annulated furanoses 9–11 in good yield and high diastereoselectivity. This protocol is a new synthetic route for the preparation of complex cyclopentanoid molecules.

  氢化三丁基锡介导的糖衍生物4–6的自由基环化使环状呋喃糖酶9–11具有较高的收率和较高的非对映选择性。该方案是用于制备复杂的环戊烷分子的新的合成途径。
• 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.