methyl (Z)-2-acetamido-3-deuterio-5-[(2-methylpropan-2-yl)oxycarbonylamino](213C)pent-2-enoate | 1136765-15-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (Z)-2-acetamido-3-deuterio-5-[(2-methylpropan-2-yl)oxycarbonylamino](213C)pent-2-enoate
• CAS: 1136765-15-5
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 288.309
• InChiKey: XFEBNBDRDSCIGM-LHPULTBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2-acetamido-3-deuterio-5-[(2-methylpropan-2-yl)oxycarbonylamino](213C)pent-2-enoate 在 (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate 、 氢气 作用下， 以 苯 为溶剂， 以84%的产率得到methyl (2S,3R)-2-acetamido-3-deuterio-5-[(2-methylpropan-2-yl)oxycarbonylamino](213C)pentanoate
  参考文献：
  名称：

  Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acid

  摘要：

  We have developed a synthetic route for (2S,3R)- and (2S,3S)-[2-C-13;3-H-2] glutamic acids with high enantioselectivity. The key reactions in this synthesis are the asymmetric reduction of the 2,3-didehydro-ornithine derivative using the (S,S)-Et-DuPHOS-Rh catalyst and the oxidation of the delta-position by ruthenium catalysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.062
• 作为产物：
  描述：

  N-Boc-3-amino[1-(2)H]propionaldehyde 、 Methyl 2-acetamido-2-[dimethoxy(oxido)phosphaniumyl]acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到methyl (Z)-2-acetamido-3-deuterio-5-[(2-methylpropan-2-yl)oxycarbonylamino](213C)pent-2-enoate
  参考文献：
  名称：

  Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acid

  摘要：

  We have developed a synthetic route for (2S,3R)- and (2S,3S)-[2-C-13;3-H-2] glutamic acids with high enantioselectivity. The key reactions in this synthesis are the asymmetric reduction of the 2,3-didehydro-ornithine derivative using the (S,S)-Et-DuPHOS-Rh catalyst and the oxidation of the delta-position by ruthenium catalysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.062

文献信息

• Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acid
  作者：Kosuke Okuma、Akira M. Ono、Seiji Tsuchiya、Makoto Oba、Kozaburo Nishiyama、Masatsune Kainosho、Tsutomu Terauchi

  DOI：10.1016/j.tetlet.2009.01.062

  日期：2009.4

  We have developed a synthetic route for (2S,3R)- and (2S,3S)-[2-C-13;3-H-2] glutamic acids with high enantioselectivity. The key reactions in this synthesis are the asymmetric reduction of the 2,3-didehydro-ornithine derivative using the (S,S)-Et-DuPHOS-Rh catalyst and the oxidation of the delta-position by ruthenium catalysis. (C) 2009 Elsevier Ltd. All rights reserved.