tert-butyl-dimethyl-[[(2R)-2-(oxan-2-yloxymethyl)oxiran-2-yl]methoxy]silane | 159002-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tert-butyl-dimethyl-[[(2R)-2-(oxan-2-yloxymethyl)oxiran-2-yl]methoxy]silane
• CAS: 159002-96-7
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: YZDAXUWVILQQBC-WUJWULDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴乙烯 、 tert-butyl-dimethyl-[[(2R)-2-(oxan-2-yloxymethyl)oxiran-2-yl]methoxy]silane 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(2S)-1-((tert-butyldimethylsilyl)oxy)-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)pent-4-en-2-ol
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 (S)-2-t-butyldimethylsilyloxymethylglycidol 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到tert-butyl-dimethyl-[[(2R)-2-(oxan-2-yloxymethyl)oxiran-2-yl]methoxy]silane
  参考文献：
  名称：

  Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

  摘要：

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.

  DOI：

  10.3987/com-08-s(f)11

文献信息

• Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative
  作者：Ken-ichi Takao、Kin-ichi Tadano、Yuki Kojima、Tomo Miyashita、Kentaro Yashiro、Tatsuya Yamada

  DOI：10.3987/com-08-s(f)11

  日期：——

  A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched alpha-acyloxy-alpha,alpha-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.