(2R,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]-5-prop-2-enyloxolan-3-ol | 956725-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]-5-prop-2-enyloxolan-3-ol
• CAS: 956725-09-0
• 化学式: C₃₂H₄₀O₅Si
• 分子量: 532.752
• InChiKey: JGPYWYQFMIGPJE-VTMRUAGOSA-N

物化性质

• 沸点：
  602.3±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]-5-prop-2-enyloxolan-3-ol 、 硫代氯甲酸苯酯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis of the ABCD Trioxadispiroketal Subunit of Azaspiracid-1:  An Iodoetherification−Dehydroiodination Strategy for Complex Spiroketals

  摘要：

  An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group.

  DOI：

  10.1021/ol701866v
• 作为产物：
  描述：

  、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[(4-methoxyphenyl)methoxy]-5-prop-2-enyloxolan-3-ol
  参考文献：
  名称：

  Synthesis of the ABCD Trioxadispiroketal Subunit of Azaspiracid-1:  An Iodoetherification−Dehydroiodination Strategy for Complex Spiroketals

  摘要：

  An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group.

  DOI：

  10.1021/ol701866v

文献信息

• Synthesis of the ABCD Trioxadispiroketal Subunit of Azaspiracid-1:  An Iodoetherification−Dehydroiodination Strategy for Complex Spiroketals
  作者：Xiaohua Li、Jialiang Li、David R. Mootoo

  DOI：10.1021/ol701866v

  日期：2007.10.1

  An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group.