{(2R,5S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl}-methanol | 219691-02-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: {(2R,5S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl}-methanol
• CAS: 219691-02-8
• 化学式: C₂₂H₄₄N₂O₄Si
• 分子量: 428.688
• InChiKey: RABYJIJHXOVOEY-NPPFBWRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.64
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {(2R,5S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl}-methanol 在 盐酸 、 三氟乙酸 作用下， 以 异丙醇 为溶剂， 以26%的产率得到(2R,3S)-2-Amino-3-hydroxy-2-hydroxymethyl-4-methyl-pentanoic acid
  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：

  ethyl (2S,5R)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-2-methylpropyl]-3,6-diethoxy-2-propan-2-yl-2H-pyrazine-5-carboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以93%的产率得到{(2R,5S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl}-methanol
  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