4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-1-O-phthalimido-D-ribo-octitol | 1057653-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-1-O-phthalimido-D-ribo-octitol
• 英文别名: 2-[3-[(2S,4S,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]propoxy]isoindole-1,3-dione
• CAS: 1057653-82-3
• 化学式: C₃₀H₃₁NO₆
• 分子量: 501.579
• InChiKey: OPAAZNGCMASNIU-SAAIGDAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-1-O-phthalimido-D-ribo-octitol 、 烯丙基三丁基锡 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 以61%的产率得到4-allyl-4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-D-erythro-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：

  N-羟基邻苯二甲酰亚胺 、 4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-D-ribo-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78%的产率得到4,7-anhydro-6,8-di-O-benzyl-2,3,5-trideoxy-1-O-phthalimido-D-ribo-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