ethyl (2S,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]-3,6-diethoxy-2-propan-2-yl-2H-pyrazine-5-carboxylate | 219691-01-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (2S,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]-3,6-diethoxy-2-propan-2-yl-2H-pyrazine-5-carboxylate
• CAS: 219691-01-7
• 化学式: C₂₅H₄₆N₂O₅Si
• 分子量: 482.736
• InChiKey: QNPGUFHPVYCFLJ-OHUGHZGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2S,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]-3,6-diethoxy-2-propan-2-yl-2H-pyrazine-5-carboxylate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-((2R,5S)-3,6-diethoxy-5-isopropyl-2-methoxymethoxymethyl-2,5-dihydro-pyrazin-2-yl)-3-methyl-but-2-enyl ester
  参考文献：
  名称：

  Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines

  摘要：

  Diastereoselective aldol-type reactions of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazine-carboxylate (5S)-3 with achiral aldehydes 8a-d was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine and MgBr2-triethylamine. The reaction with Sn(II) between (5S)-3 and aliphatic aldehydes 8a,b proved to be quite different from that with Mg(II). On the other hand, Sn(II)- or Mg(II)-mediated aldol-type reactions of (5S)-3 with benzaldehyde Sc and 3-methyl-2-butenal 8d each afforded the same diastereomer as the major product. These aldol products were each converted to the corresponding alpha-substituted serines 6 and 7 as enantiomerically pure compounds. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00371-1
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 叔丁基二甲硅基三氟甲磺酸酯 、 2,5-Bisethoxy-3-ethoxycarbonyl-6-isopropyl-3,6-dihydropyrazin 在 2,6-二甲基吡啶 、 三乙胺 、 magnesium bromide 作用下， 生成 、 ethyl (2S,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]-3,6-diethoxy-2-propan-2-yl-2H-pyrazine-5-carboxylate 、 、
  参考文献：
  名称：

  Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines

  摘要：

  Diastereoselective aldol-type reactions of ethyl (5S)-3,6-diethoxy-2,5-dihydro-5-isopropyl-2-pyrazine-carboxylate (5S)-3 with achiral aldehydes 8a-d was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine and MgBr2-triethylamine. The reaction with Sn(II) between (5S)-3 and aliphatic aldehydes 8a,b proved to be quite different from that with Mg(II). On the other hand, Sn(II)- or Mg(II)-mediated aldol-type reactions of (5S)-3 with benzaldehyde Sc and 3-methyl-2-butenal 8d each afforded the same diastereomer as the major product. These aldol products were each converted to the corresponding alpha-substituted serines 6 and 7 as enantiomerically pure compounds. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00371-1