1-O-benzyl 2-O-methyl (2S,3R)-3-[(1S)-1,2-dimethoxy-2-oxoethyl]aziridine-1,2-dicarboxylate | 494847-12-0

• 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: 1-O-benzyl 2-O-methyl (2S,3R)-3-[(1S)-1,2-dimethoxy-2-oxoethyl]aziridine-1,2-dicarboxylate
• CAS: 494847-12-0
• 化学式: C₁₆H₁₉NO₇
• 分子量: 337.329
• InChiKey: SVOHWBOBRWBDAF-LKKKIQRRSA-N

物化性质

• 沸点：
  452.3±45.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-benzyl 2-O-methyl (2S,3R)-3-[(1S)-1,2-dimethoxy-2-oxoethyl]aziridine-1,2-dicarboxylate 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 甲苯 、 苯甲醇 为溶剂， 反应 6.25h， 生成 (2S,3S,4S)-3,4-dimethoxyglutamic acid
  参考文献：
  名称：

  Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone

  摘要：

  The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-gamma-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the beta-position. A key step of the strategy was a titanate-mediated transesterification of a dimethyl ester into a dibenzyl analogue, allowing efficient deprotection to the free amino acid by hydrogenolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01762-8
• 作为产物：
  描述：

  6-O-benzyl 2-O-methyl (1R,2S,5S)-4-oxo-3-oxa-6-azabicyclo[3.1.0]hexane-2,6-dicarboxylate 在 calcium sulfate 、 三氟化硼乙醚 、 silver(l) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-O-benzyl 2-O-methyl (2S,3R)-3-[(1S)-1,2-dimethoxy-2-oxoethyl]aziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Enantiospecific synthesis of 3,4-disubstituted glutamic acids via controlled stepwise ring-opening of 2,3-aziridino-γ-lactone

  摘要：

  The preparation of enantiomerically pure 3,4-disubstituted glutamic acids is described starting from D-ribose. This preparation involved the use of a 2,3-aziridino-gamma-lactone whose reactivity towards nucleophiles could be efficiently controlled to allow selective functionalization at the beta-position. A key step of the strategy was a titanate-mediated transesterification of a dimethyl ester into a dibenzyl analogue, allowing efficient deprotection to the free amino acid by hydrogenolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01762-8