1-[(2R,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-one | 201683-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(2R,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-one
• 英文别名: 3-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-1-[(2R,3S)-2-methyl-3-[(2S)-6-phenylmethoxyhexan-2-yl]oxiran-2-yl]propan-1-one
• CAS: 201683-56-9
• 化学式: C₂₇H₄₆O₄Si
• 分子量: 462.745
• InChiKey: FWGUOHGODIZEIC-JEYPMZLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-one 在 2,6-二甲基吡啶 、 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R,5S,6S)-10-Benzyloxy-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,2,4,6-tetramethyl-decan-3-one
  参考文献：
  名称：

  Radical-induced Opening of Trisubstituted Epoxides: Application in the Synthesis of C1–C12 Segment of Epothilones

  摘要：

  Diastereo- and regioselective opening of a trisubstituted epoxy ketone at the more substituted carbon using samarium(II) iodide presents an alternate approach to the C-5-C-7 aldol moiety with beta-hydroxyketo framework in the stereoselective synthesis of C-1-C-12 segment of epothilones. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10442-7
• 作为产物：
  描述：

  methyl 3-hydroxy-2,2-dimethyl-3-[(2S,3S)-2-methyl-3-[(2S)-6-phenylmethoxyhexan-2-yl]oxiran-2-yl]propanoate 在 锂硼氢 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-[(2R,3S)-3-((S)-5-Benzyloxy-1-methyl-pentyl)-2-methyl-oxiranyl]-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propan-1-one
  参考文献：
  名称：

  Radical-induced Opening of Trisubstituted Epoxides: Application in the Synthesis of C1–C12 Segment of Epothilones

  摘要：

  Diastereo- and regioselective opening of a trisubstituted epoxy ketone at the more substituted carbon using samarium(II) iodide presents an alternate approach to the C-5-C-7 aldol moiety with beta-hydroxyketo framework in the stereoselective synthesis of C-1-C-12 segment of epothilones. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10442-7

文献信息

• Radical-induced Opening of Trisubstituted Epoxides: Application in the Synthesis of C1–C12 Segment of Epothilones
  作者：T.K Chakraborty、S Dutta

  DOI：10.1016/s0040-4039(97)10442-7

  日期：1998.1

  Diastereo- and regioselective opening of a trisubstituted epoxy ketone at the more substituted carbon using samarium(II) iodide presents an alternate approach to the C-5-C-7 aldol moiety with beta-hydroxyketo framework in the stereoselective synthesis of C-1-C-12 segment of epothilones. (C) 1997 Elsevier Science Ltd. All rights reserved.