5-O-benzyl-3-C-cyano-1,2-O-isopropylidene-3-O-methoxymethylphosphonyl-α-D-ribofuranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzyl-3-C-cyano-1,2-O-isopropylidene-3-O-methoxymethylphosphonyl-α-D-ribofuranose
• 英文别名: (3aR,5R,6R,6aR)-6-(methoxy-methyl-oxidophosphaniumyl)oxy-2,2-dimethyl-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6-carbonitrile
• 化学式: C₁₈H₂₄NO₇P
• 分子量: 397.365
• InChiKey: RHJWLWLYVIBDRF-MKMAAYBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 在 4-二甲氨基吡啶 、 碳酸氢钠 作用下， 以 吡啶 、 乙醚 、 水 为溶剂， 反应 1.0h， 生成 5-O-benzyl-3-C-cyano-1,2-O-isopropylidene-3-O-methoxymethylphosphonyl-α-D-ribofuranose
  参考文献：
  名称：

  Preparation of Spiro[4.4]oxaphospholene and -azaphospholene Systems from Carbohydrate Templates

  摘要：

  Introduction of a spiro-phosphorus cycle in position 3 of monosaccharidic derivatives was studied starting from cyanohydrin or aminonitrile A. A two-step procedure involving (i) phosphonylation and (ii) carbanion-mediated phosphonate intramolecular cyclization (denoted CPIC) was used. The necessity of having an electron-withdrawing group alpha to the phosphorus atom in order to avoid undesired reactions was demonstrated.

  DOI：

  10.1021/jo400954p

文献信息

• Preparation of Spiro[4.4]oxaphospholene and -azaphospholene Systems from Carbohydrate Templates
  作者：Marina Moura、Solen Josse、Denis Postel

  DOI：10.1021/jo400954p

  日期：2013.9.20

  Introduction of a spiro-phosphorus cycle in position 3 of monosaccharidic derivatives was studied starting from cyanohydrin or aminonitrile A. A two-step procedure involving (i) phosphonylation and (ii) carbanion-mediated phosphonate intramolecular cyclization (denoted CPIC) was used. The necessity of having an electron-withdrawing group alpha to the phosphorus atom in order to avoid undesired reactions was demonstrated.