(2S,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[(2S,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-2-pentyloxolan-3-yl]-2-pentyloxolan-3-one | 1092556-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[(2S,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-2-pentyloxolan-3-yl]-2-pentyloxolan-3-one
• CAS: 1092556-30-3
• 化学式: C₃₂H₆₄O₆Si₂
• 分子量: 601.028
• InChiKey: MGZKPAPXVQGJEI-JRAUOLTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.03
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (-)-(2R,3R,4R,5S)-2-(tert-butyldimethylsilyloxymethyl)-3,4-epoxy-5-pentyl-4-(p-tolylsulfonyl)tetrahydrofuran 在 magnesium iodide 作用下， 以 乙醚 为溶剂， 反应 36.0h， 以92%的产率得到(-)-(2S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2-pentyl-3-oxotetrahydrofuran
  参考文献：
  名称：

  Highly Diastereoselective Katsuki−Jacobsen Oxidation−Epoxidation of α-Silyloxy Sulfinyl Dienes: Synthetic Applications

  摘要：

  Katsuki-Jacobsen oxidation-epoxidation of acyclic alpha-silyloxy sulfinyl dienes, followed by acid-promoted cyclization, leads to 2,5-trans-sulfonyl dihydrofurans with good selectivities. As an application, the formal syntheses of (6S,7S,9R,10R)- and (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diols is reported.

  DOI：

  10.1021/jo801803m

文献信息

• Highly Diastereoselective Katsuki−Jacobsen Oxidation−Epoxidation of α-Silyloxy Sulfinyl Dienes: Synthetic Applications
  作者：Roberto Fernández de la Pradilla、Alejandro Castellanos、Iñaki Osante、Ignacio Colomer、Mateo I. Sánchez

  DOI：10.1021/jo801803m

  日期：2009.1.2

  Katsuki-Jacobsen oxidation-epoxidation of acyclic alpha-silyloxy sulfinyl dienes, followed by acid-promoted cyclization, leads to 2,5-trans-sulfonyl dihydrofurans with good selectivities. As an application, the formal syntheses of (6S,7S,9R,10R)- and (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diols is reported.