(Z)-3-O-(triphenylmethyl)-1-(trimethylsilyl)prop-1-en-3-ol | 144242-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (Z)-3-O-(triphenylmethyl)-1-(trimethylsilyl)prop-1-en-3-ol
• 英文别名: trimethyl-[(Z)-3-trityloxyprop-1-enyl]silane
• CAS: 144242-26-2
• 化学式: C₂₅H₂₈OSi
• 分子量: 372.582
• InChiKey: ZZRMGKZTOJPDRH-BKUYFWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-O-(triphenylmethyl)-1-(trimethylsilyl)prop-1-en-3-ol 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以91%的产率得到(1R*,2S*)-1,2-epoxy-3-O-(triphenylmethyl)-1-(trimethylsilyl)propan-3-ol
  参考文献：
  名称：

  Synthesis of four stereoisomeric tetrose derivatives from propargyl alcohol. One-carbon homologation of vinylsilanes via .alpha.,.beta.-epoxy silanes

  摘要：

  Silicon-mediated synthesis of stereoisomeric tetroses 1, 2, 3, and 4, from propargyl alcohol, is described. An allylic alcohol bearing the trimethylsilyl group in the gamma-position, rac-9b, was subjected to the Sharpless kinetic resolution to give (2S)-9b and the (2S,3S,4S)-epoxide 10a of very high enantiomeric purity (greater-than-or-equal-to 97% ee). Compound (2S)-9b was epoxidized with tert-butyl hydroperoxide and vanadyl acetylacetonate to give epoxide 14a as the major product. Epoxy silanes 10a and 14a were treated with benzenethiol in the presence of silica gel to give the corresponding sulfides (11a and 16a). Sulfides 11b and 16b were oxidized to sulfoxides which, without isolation, were subjected to the Pummerer rearrangement followed by hydrolysis. Intermediate vinylsilane 9a was prepared from vinylsilane 6 via epoxy silane 7 using a novel homologation method.

  DOI：

  10.1021/jo00050a041
• 作为产物：
  描述：

  1-trityloxy-2-propyne 在 N-甲基吗啉 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 (Z)-3-O-(triphenylmethyl)-1-(trimethylsilyl)prop-1-en-3-ol
  参考文献：
  名称：

  Synthesis of four stereoisomeric tetrose derivatives from propargyl alcohol. One-carbon homologation of vinylsilanes via .alpha.,.beta.-epoxy silanes

  摘要：

  Silicon-mediated synthesis of stereoisomeric tetroses 1, 2, 3, and 4, from propargyl alcohol, is described. An allylic alcohol bearing the trimethylsilyl group in the gamma-position, rac-9b, was subjected to the Sharpless kinetic resolution to give (2S)-9b and the (2S,3S,4S)-epoxide 10a of very high enantiomeric purity (greater-than-or-equal-to 97% ee). Compound (2S)-9b was epoxidized with tert-butyl hydroperoxide and vanadyl acetylacetonate to give epoxide 14a as the major product. Epoxy silanes 10a and 14a were treated with benzenethiol in the presence of silica gel to give the corresponding sulfides (11a and 16a). Sulfides 11b and 16b were oxidized to sulfoxides which, without isolation, were subjected to the Pummerer rearrangement followed by hydrolysis. Intermediate vinylsilane 9a was prepared from vinylsilane 6 via epoxy silane 7 using a novel homologation method.

  DOI：

  10.1021/jo00050a041

文献信息

• Synthesis of four stereoisomeric tetrose derivatives from propargyl alcohol. One-carbon homologation of vinylsilanes via .alpha.,.beta.-epoxy silanes
  作者：Barbara Achmatowicz、Piotr Raubo、Jerzy Wicha

  DOI：10.1021/jo00050a041

  日期：1992.11

  Silicon-mediated synthesis of stereoisomeric tetroses 1, 2, 3, and 4, from propargyl alcohol, is described. An allylic alcohol bearing the trimethylsilyl group in the gamma-position, rac-9b, was subjected to the Sharpless kinetic resolution to give (2S)-9b and the (2S,3S,4S)-epoxide 10a of very high enantiomeric purity (greater-than-or-equal-to 97% ee). Compound (2S)-9b was epoxidized with tert-butyl hydroperoxide and vanadyl acetylacetonate to give epoxide 14a as the major product. Epoxy silanes 10a and 14a were treated with benzenethiol in the presence of silica gel to give the corresponding sulfides (11a and 16a). Sulfides 11b and 16b were oxidized to sulfoxides which, without isolation, were subjected to the Pummerer rearrangement followed by hydrolysis. Intermediate vinylsilane 9a was prepared from vinylsilane 6 via epoxy silane 7 using a novel homologation method.