5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-(2,5-dioxopyrrolidine)-α-D-ribofuranose | 1355965-96-6

• 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-3-deoxy-1,2-O-isopropylidene-3-(2,5-dioxopyrrolidine)-α-D-ribofuranose
• 英文别名: (3aR,5S,6R,6aR)-6-(2,5-dioxopyrrolidin-1-yl)-2,2-dimethyl-5-(phenylmethoxymethyl)-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-6-carbonitrile
• CAS: 1355965-96-6
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: QKURFUBGYYOLPZ-GVZBARQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-(2,5-dioxopyrrolidine)-α-D-ribofuranose 、 乙基溴化镁 在 METHYLTITANIUM TRIISOPROPOXIDE 、 三氟化硼乙醚 、 盐酸 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.0h， 以23%的产率得到spiro[5-O-benzyl-3-deoxy-1,2-isopropylidene-α-D-ribofuranose-3,3'-(2'-ethylidene-3',6',7'-trihydro-5'-oxo-pyrrolo[1,2-a]imidazole)]
  参考文献：
  名称：

  Reactivity of sugar α-aminonitrile derivatives under titanium-mediated cyclopropanation conditions

  摘要：

  The reactivity of different sugar alpha-aminonitriles has been studied under titanium-mediated cyclo-propanation conditions. This study has been performed on amide, lactam, and imide derivatives. It has been possible to obtain spiro[furanose-3,3'-(3',5',6',7'-tetrahydrospiro[cyclopropane-1,2'-pyrrolo[1,2-a] imidazole])] derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.067
• 作为产物：
  描述：

  5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 titanium(IV) isopropylate 、 氯化亚砜 、 氨 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-(2,5-dioxopyrrolidine)-α-D-ribofuranose
  参考文献：
  名称：

  Reactivity of sugar α-aminonitrile derivatives under titanium-mediated cyclopropanation conditions

  摘要：

  The reactivity of different sugar alpha-aminonitriles has been studied under titanium-mediated cyclo-propanation conditions. This study has been performed on amide, lactam, and imide derivatives. It has been possible to obtain spiro[furanose-3,3'-(3',5',6',7'-tetrahydrospiro[cyclopropane-1,2'-pyrrolo[1,2-a] imidazole])] derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.067

文献信息

• Reactivity of sugar α-aminonitrile derivatives under titanium-mediated cyclopropanation conditions
  作者：Delphine Declerck、Solen Josse、Albert Nguyen Van Nhien、Jan Szymoniak、Philippe Bertus、Denis Postel

  DOI：10.1016/j.tet.2011.11.067

  日期：2012.1

  The reactivity of different sugar alpha-aminonitriles has been studied under titanium-mediated cyclo-propanation conditions. This study has been performed on amide, lactam, and imide derivatives. It has been possible to obtain spiro[furanose-3,3'-(3',5',6',7'-tetrahydrospiro[cyclopropane-1,2'-pyrrolo[1,2-a] imidazole])] derivatives. (C) 2011 Elsevier Ltd. All rights reserved.