(E)-ethyl 2,3,4-trideoxy-D-gluco-oct-2-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 2,3,4-trideoxy-D-gluco-oct-2-enoate
• 英文别名: ethyl (E,5R,6S,7R)-5,6,7,8-tetrahydroxyoct-2-enoate
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: IIPXQOYBBOYHGN-ZQGGKVLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2,3,4-trideoxy-D-gluco-oct-2-enoate 、 N,O-双(三甲基硅基)氨基甲酸 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 生成 (E)-ethyl 2,3,4-trideoxy-5,6,7,8-tetra-O-trimethylsilyl-D-gluco-oct-2-enoate
  参考文献：
  名称：

  A straightforward synthesis of glyco-2,7- and 2,8-dienes

  摘要：

  In this paper, we report the efficient preparation of carbohydrate-derived 2,7- and 2,8-dienes. By our synthetic approach, we have quickly converted D-glucose 1 to (E)-ethyl-2,3-dideoxy-D-gluco-oct-2-enoate 5, which led to the desired (E)-ethyl-9,9-dibromo-2,3,8,9-tetradeoxy-4,5,6,7-tetra-(E)-trimethylsilyl-D-gluco-nona-2,8-dienoate 19 with satisfying yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.057
• 作为产物：
  描述：

  2-Deoxy-D-glucose 、 溴乙酸乙酯 在 三丁基膦 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 以80%的产率得到(E)-ethyl 2,3,4-trideoxy-D-gluco-oct-2-enoate
  参考文献：
  名称：

  A straightforward synthesis of glyco-2,7- and 2,8-dienes

  摘要：

  In this paper, we report the efficient preparation of carbohydrate-derived 2,7- and 2,8-dienes. By our synthetic approach, we have quickly converted D-glucose 1 to (E)-ethyl-2,3-dideoxy-D-gluco-oct-2-enoate 5, which led to the desired (E)-ethyl-9,9-dibromo-2,3,8,9-tetradeoxy-4,5,6,7-tetra-(E)-trimethylsilyl-D-gluco-nona-2,8-dienoate 19 with satisfying yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.057

文献信息

• A straightforward synthesis of glyco-2,7- and 2,8-dienes
  作者：Franck Dolhem、Nicolas Smiljanic、Catherine Lièvre、Gilles Demailly

  DOI：10.1016/j.tet.2006.05.057

  日期：2006.8

  In this paper, we report the efficient preparation of carbohydrate-derived 2,7- and 2,8-dienes. By our synthetic approach, we have quickly converted D-glucose 1 to (E)-ethyl-2,3-dideoxy-D-gluco-oct-2-enoate 5, which led to the desired (E)-ethyl-9,9-dibromo-2,3,8,9-tetradeoxy-4,5,6,7-tetra-(E)-trimethylsilyl-D-gluco-nona-2,8-dienoate 19 with satisfying yield. (c) 2006 Elsevier Ltd. All rights reserved.