4,7-anhydro-2,3-dideoxy-5,6,8-tri-O-methyl-D-allo-octitol | 1057653-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,7-anhydro-2,3-dideoxy-5,6,8-tri-O-methyl-D-allo-octitol
• CAS: 1057653-76-5
• 化学式: C₁₁H₂₂O₅
• 分子量: 234.293
• InChiKey: FAWICWIKCWVKSH-ZRUFSTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 4,7-anhydro-2,3-dideoxy-5,6,8-tri-O-methyl-D-allo-octitol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到4,7-anhydro-2,3-dideoxy-5,6,8-tri-O-methyl-1-O-phthalimido-D-allo-octitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070
• 作为产物：
  描述：

  3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)prop-1-ene 、 碘甲烷 以71%的产率得到4,7-anhydro-2,3-dideoxy-5,6,8-tri-O-methyl-D-allo-octitol
  参考文献：
  名称：

  Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

  摘要：

  A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.070