(1S)-1-[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-pentyloxolan-2-yl]dec-9-en-1-ol | 1053443-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-pentyloxolan-2-yl]dec-9-en-1-ol
• CAS: 1053443-61-0
• 化学式: C₂₅H₅₀O₃Si
• 分子量: 426.756
• InChiKey: XMVYBVOHYRCOLT-XQUALCHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-pentyloxolan-2-yl]dec-9-en-1-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以100%的产率得到(6S,7S,9R,10S)-6,9-epoxynonadec-18-en-7,10-diol
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h
• 作为产物：
  描述：

  (S)-1-[4-((S)-2-Hydroxy-dec-4-ynyloxy)-phenoxy]-dec-4-yn-2-ol 在 potassium osmate 、 lithium aluminium tetrahydride 、 草酰氯 、 ammonium cerium(IV) nitrate 、 K₂OsO₂(OH)4,DHQ)2PHAL 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二乙二醇二甲醚 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 124.08h， 生成 (1S)-1-[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-pentyloxolan-2-yl]dec-9-en-1-ol
  参考文献：
  名称：

  Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

  摘要：

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.

  DOI：

  10.1021/jo971324h

文献信息

• Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6<i>S</i>,7<i>S</i>,9<i>R</i>,10<i>R</i>)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product
  作者：Zhi-Min Wang、Ming Shen

  DOI：10.1021/jo971324h

  日期：1998.3.1

  An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C-3 building block 5 as-the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol(1), was successfully synthesized in high enantioselectivity.