[(2S,3aR,7aR)-5-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3a,7,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]methoxy-tert-butyl-diphenylsilane | 956725-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: [(2S,3aR,7aR)-5-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3a,7,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 956725-13-6
• 化学式: C₃₄H₄₂O₅Si
• 分子量: 558.79
• InChiKey: VBGNZWFSDUQMGF-PHCUSUGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3aR,7aR)-5-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3a,7,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]methoxy-tert-butyl-diphenylsilane 、 二碘甲烷 在 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%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：

  tert-butyl-[[(2S,4R,5R)-4-[4-[(4-methoxyphenyl)methoxy]but-1-en-2-yloxy]-5-prop-2-enyloxolan-2-yl]methoxy]-diphenylsilane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到[(2S,3aR,7aR)-5-[2-[(4-methoxyphenyl)methoxy]ethyl]-3,3a,7,7a-tetrahydro-2H-furo[3,2-b]pyran-2-yl]methoxy-tert-butyl-diphenylsilane
  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