dibenzyl (2S,3S,4S)-2,3-dimethoxy-4-(phenylmethoxycarbonylamino)pentanedioate | 494847-16-4

• 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: dibenzyl (2S,3S,4S)-2,3-dimethoxy-4-(phenylmethoxycarbonylamino)pentanedioate
• CAS: 494847-16-4
• 化学式: C₂₉H₃₁NO₈
• 分子量: 521.567
• InChiKey: FGMPTQOTHKNPFB-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dibenzyl (2S,3S,4S)-2,3-dimethoxy-4-(phenylmethoxycarbonylamino)pentanedioate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到(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：

  1-O-benzyl 2-O-methyl (2S,3R)-3-[(1S)-1-hydroxy-2-methoxy-2-oxoethyl]aziridine-1,2-dicarboxylate 在 calcium sulfate 、 三氟化硼乙醚 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲苯 、 苯甲醇 为溶剂， 反应 20.25h， 生成 dibenzyl (2S,3S,4S)-2,3-dimethoxy-4-(phenylmethoxycarbonylamino)pentanedioate
  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