(+)-(2S,3S,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyltetrahydrofuran | 1092556-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2S,3S,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyltetrahydrofuran
• 英文别名: [(2S,3S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-pentyloxolan-3-yl] benzoate
• CAS: 1092556-29-0
• 化学式: C₂₃H₃₈O₄Si
• 分子量: 406.638
• InChiKey: JCUWLMFTSRDHHC-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(2S,3S,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyltetrahydrofuran 在 Dowex resin 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84%的产率得到5-hydroxymethyl-2-pentyl-3-phenylcarbonyloxy-(2S,3S,5S)-tetrahydrofuran
  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
• 作为产物：
  描述：

  (+)-(2S,3S,5S)-5-(tert-butyldimethylsilyloxymethyl)-2-pentyl-tetrahydrofuran-3-ol 、 苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以95%的产率得到(+)-(2S,3S,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-phenylcarbonyloxy-2-pentyltetrahydrofuran
  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.