tert-butyl (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonyl)aminopropionate | 765299-31-8

• 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: tert-butyl (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonyl)aminopropionate
• CAS: 765299-31-8
• 化学式: C₂₁H₃₂N₂O₆
• 分子量: 408.495
• InChiKey: NRYXTDXIPFETCK-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonyl)aminopropionate 在 sodium hydroxide 、 sodium carbonate 、 三氟乙酸 作用下， 以 叔丁醇 为溶剂， 反应 5.0h， 生成 (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonylamino)propionic acid
  参考文献：
  名称：

  First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

  摘要：

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.034
• 作为产物：
  描述：

  叔丁醇 、 N-Z-N-Me-Asp-O-t-Bu 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 反应 17.0h， 以49%的产率得到tert-butyl (S)-2-(N-benzyloxycarbonyl-N-methyl)amino-3-(tert-butoxycarbonyl)aminopropionate
  参考文献：
  名称：

  First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

  摘要：

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.034