(2R,3S,4R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-4-phenoxythiocarbonyloxy-tetrahydrofuran-3-yl benzoate | 550316-66-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-4-phenoxythiocarbonyloxy-tetrahydrofuran-3-yl benzoate
• CAS: 550316-66-0
• 化学式: C₂₇H₃₀O₆S
• 分子量: 482.598
• InChiKey: HFPMMZMNZPVNAT-PNDAWPNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-4-phenoxythiocarbonyloxy-tetrahydrofuran-3-yl benzoate 在 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 生成 (2R,3R)-5-hydroxy-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,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl benzoate 在 吡啶 、 4-二甲氨基吡啶 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2R,3S,4R)-5-methoxy-2-[octa-2(Z),5(E)-dienyl]-4-phenoxythiocarbonyloxy-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