(1S,2R,4'S)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylic acid | 194728-69-3

• 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: (1S,2R,4'S)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylic acid
• CAS: 194728-69-3
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: LXENFXSFHJMYDJ-AHIWAGSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,4'S)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylic acid 在 盐酸 、 sodium periodate 、 Ru₂O hydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 34.5h， 生成 methyl (1S,2R)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-carboxycyclopropyl-1-carbonyl-N-((R)-2-phenylglycinate)
  参考文献：
  名称：

  Enantioselective synthesis of novel, highly conformationally constrained peptide surrogates

  摘要：

  Two new enantiomeric peptide surrogates as well as a tripeptide, ail of them having highly conformationally constrained structures, have been synthesized. (Z)-cyclo-Aspartic acid and convenient a-substituted isoserine derivatives, in both antipodal forms, as well as methyl (R)-2-phenylglycinate, have been used as the monomeric units. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00265-6
• 作为产物：
  描述：

  methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以90%的产率得到(1S,2R,4'S)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  Enantioselective synthesis of novel, highly conformationally constrained peptide surrogates

  摘要：

  Two new enantiomeric peptide surrogates as well as a tripeptide, ail of them having highly conformationally constrained structures, have been synthesized. (Z)-cyclo-Aspartic acid and convenient a-substituted isoserine derivatives, in both antipodal forms, as well as methyl (R)-2-phenylglycinate, have been used as the monomeric units. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00265-6

文献信息

• Enantioselective synthesis of novel, highly conformationally constrained peptide surrogates
  作者：Miguel Díaz、JoséM. Jiménez、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(97)00265-6

  日期：1997.7

  Two new enantiomeric peptide surrogates as well as a tripeptide, ail of them having highly conformationally constrained structures, have been synthesized. (Z)-cyclo-Aspartic acid and convenient a-substituted isoserine derivatives, in both antipodal forms, as well as methyl (R)-2-phenylglycinate, have been used as the monomeric units. (C) 1997 Elsevier Science Ltd.