(4S,5R)-5-[(2S,5S,6R)-2,5-dihydroxy-2,6-dimethyloct-7-enyl]-4-ethenyloxolan-2-one | 1224633-06-0

• 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: (4S,5R)-5-[(2S,5S,6R)-2,5-dihydroxy-2,6-dimethyloct-7-enyl]-4-ethenyloxolan-2-one
• CAS: 1224633-06-0
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: WSINXVGGGXFHEZ-SSZWKKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-[(2S,5S,6R)-2,5-dihydroxy-2,6-dimethyloct-7-enyl]-4-ethenyloxolan-2-one 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(4S,5R)-5-[(2S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-2,6-dimethyloct-7-enyl]-4-ethenyloxolan-2-one
  参考文献：
  名称：

  Second-generation total synthesis of (−)-diversifolin

  摘要：

  A second-generation total synthesis of (-)-diversifolin has been achieved by a more straightforward strategy. involving a highly stereochemistry-dependent 10-membered ring-closing metathesis and a stereoselective dihydroxylation/lactone transposition sequence. Compared to Our previous synthesis, the present synthesis is improved in the yield of the key intermediate 2 (20% in 12 steps from diol 8). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.012
• 作为产物：
  描述：

  (4S,5R)-4-ethenyl-5-[(2S,5S,6R)-5-hydroxy-2,6-dimethyl-2-trimethylsilyloxyoct-7-enyl]oxolan-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到(4S,5R)-5-[(2S,5S,6R)-2,5-dihydroxy-2,6-dimethyloct-7-enyl]-4-ethenyloxolan-2-one
  参考文献：
  名称：

  Second-generation total synthesis of (−)-diversifolin

  摘要：

  A second-generation total synthesis of (-)-diversifolin has been achieved by a more straightforward strategy. involving a highly stereochemistry-dependent 10-membered ring-closing metathesis and a stereoselective dihydroxylation/lactone transposition sequence. Compared to Our previous synthesis, the present synthesis is improved in the yield of the key intermediate 2 (20% in 12 steps from diol 8). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.012

文献信息

• Second-generation total synthesis of (−)-diversifolin
  作者：Kazuma Tsuboi、Tomoaki Nakamura、Takahiro Suzuki、Atsuo Nakazaki、Susumu Kobayashi

  DOI：10.1016/j.tetlet.2010.02.012

  日期：2010.4

  A second-generation total synthesis of (-)-diversifolin has been achieved by a more straightforward strategy. involving a highly stereochemistry-dependent 10-membered ring-closing metathesis and a stereoselective dihydroxylation/lactone transposition sequence. Compared to Our previous synthesis, the present synthesis is improved in the yield of the key intermediate 2 (20% in 12 steps from diol 8). (C) 2010 Elsevier Ltd. All rights reserved.