methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate | 171513-98-7

• 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 (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate
• 英文别名: (2S,3R)-Cbz-cyclo-Asp-OMe
• CAS: 171513-98-7
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: PHTJBBNDQDSSRJ-HZMBPMFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate 在 氯化亚砜 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 29.5h， 生成 methyl (1S,2S)-2-(2-methoxy-2-oxoethyl)-1-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylate
  参考文献：
  名称：

  First enantioselective synthesis of (−)-(Z)-2,3-methano-L-glutamic acid

  摘要：

  (-)-(Z)-2,3-甲基-L-谷氨酸，作为一种潜在的mGluR激动剂，首次以40%的总收率从一种易于获得的同源手性氨基戊烯酸酯前体中成功合成。本研究中的关键中间体是一种便于保护的(-)-(Z)-环状天冬氨酸衍生物，而羧酸的同系化则通过Arndt-Eistert程序完成。版权©1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00423-5
• 作为产物：
  描述：

  (±)-Z-α-膦酰甘氨酸三甲酯 在 盐酸 、 甲醇 、 sodium periodate 、 重铬酸吡啶 、 二苯甲酮 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 160.63h， 生成 methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-carboxycyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9

文献信息

• Enantioselective synthesis of novel homochiral α-substituted (S)-isoserine derivatives. Incorporation of this amino acid in a highly conformationally constrained dipeptide surrogate
  作者：Miguel Díaz、Rosa M Ortuño

  DOI：10.1016/s0957-4166(96)00454-5

  日期：1996.12

  Optically pure isoserine derivatives with a chiral polyfunctional bicyclo[3.1.0]hexyl substituent at the α-carboxyl position were synthesized from a common cyclopentene precursor bearing an α-epoxy ester function in a side-chain. Cyclopropanation of the double bond and nucleophilic oxirane-ring opening by using a homochiral amine were the key steps. One of the synthesized derivatives was condensed

  由在侧链上具有α-环氧酯功能的普通环戊烯前体合成了在α-羧基位置具有手性多官能双环双环[3.1.0]己基取代基的光学纯的异丝氨酸衍生物。关键步骤是通过使用手性胺对双键进行环丙烷化和亲核环氧乙烷环的开环。将合成的衍生物之一与Cbz-环-Asp-OMe缩合，得到高度构象约束的二肽替代物。
• Enantioselective total syntheses of (−)-allo-coronamic acid, (−)-(Z)-2,3-methanohomoserine, and (2S,3R)-Cbz-cyclo-Asp-OMe
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(95)00234-g

  日期：1995.8

  The title amino acids have been synthesized in 45, 47, and 63% overall yields, respectively, from enantiopure aminopentenoates, easily available from D-glyceraldehyde as a source of chirality, following divergent pathways from similar diols as common key intermediate compounds.
• 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.
• Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(96)00038-9

  日期：1996.2

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.
• First enantioselective synthesis of (−)-(Z)-2,3-methano-L-glutamic acid
  作者：JoséM. Jiménez、Rosa M. Ortuño

  DOI：10.1016/0957-4166(96)00423-5

  日期：1996.11

  (-)-(Z)-2,3-Methano-L-glutamic acid, a potential mGluR agonist, has been synthesized for the first time in 40% overall yield from a homochiral amino pentenoate as an easily available precursor. A conveniently protected (-)-(Z)-cyclo-aspartic acid derivative was the key intermediate, homologation of the carboxylic acid having been accomplished via the Arndt-Eistert procedure. Copyright (C) 1996 Elsevier Science Ltd

  (-)-(Z)-2,3-甲基-L-谷氨酸，作为一种潜在的mGluR激动剂，首次以40%的总收率从一种易于获得的同源手性氨基戊烯酸酯前体中成功合成。本研究中的关键中间体是一种便于保护的(-)-(Z)-环状天冬氨酸衍生物，而羧酸的同系化则通过Arndt-Eistert程序完成。版权©1996 Elsevier Science Ltd