(2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate | 550316-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate
• 英文别名: [(2R,3R,4R)-4-hydroxy-5-methoxy-2-[(2Z,5E)-octa-2,5-dienyl]oxolan-3-yl] benzoate
• CAS: 550316-65-9
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: PXAATZUVYINBDZ-VTKQUKSTSA-N

物化性质

• 沸点：
  478.9±45.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (2R,3R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors

  摘要：

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00078-8
• 作为产物：
  描述：

  (3aR,3bS,6aR,7aR)-2,2-dimethyl-hexahydrofuro[2',3':4,5]furo[2,3-d][1,3]dioxol-5-ol 在 吡啶 、 双(三甲基硅烷基)氨基钾 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 15.0h， 生成 (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors

  摘要：

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00078-8

文献信息

• Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors
  作者：Rajendrakumar Reddy Gadikota、Adam I. Keller、Christopher S. Callam、Todd L. Lowary

  DOI：10.1016/s0957-4166(03)00078-8

  日期：2003.3

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.