(L)-methyl 3-(4-methoxybenzylamino)-2-(4-methylphenylsulfonamido)propanoate | 1429195-00-5

• 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: (L)-methyl 3-(4-methoxybenzylamino)-2-(4-methylphenylsulfonamido)propanoate
• 英文别名: (S)-methyl 3-(4-methoxybenzylamino)-2-(4-methylphenylsulfonamido)propanoate；methyl (2S)-3-[(4-methoxyphenyl)methylamino]-2-[(4-methylphenyl)sulfonylamino]propanoate
• CAS: 1429195-00-5
• 化学式: C₁₉H₂₄N₂O₅S
• 分子量: 392.476
• InChiKey: MATDQPCCLUTHQM-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(p-nosyl)aziridine-2R-carboxylic acid methyl ester 、 (L)-methyl 3-(4-methoxybenzylamino)-2-(4-methylphenylsulfonamido)propanoate 以 乙腈 为溶剂， 反应 24.0h， 以32%的产率得到(S)-allyl 3-(((R)-3-methoxy-2-(4-nitrophenylsulfonamido)-3-oxopropyl)(4-methoxybenzyl)amino)-2-((4-nitrobenzyloxy)carbonylamino)propanoate
  参考文献：
  名称：

  Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

  摘要：

  Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding beta-methyl azalanthionines have, so far, been unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.011
• 作为产物：
  描述：

  对甲苯磺酰氯 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 48.0h， 生成 (L)-methyl 3-(4-methoxybenzylamino)-2-(4-methylphenylsulfonamido)propanoate
  参考文献：
  名称：

  Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

  摘要：

  Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding beta-methyl azalanthionines have, so far, been unsuccessful. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.011

文献信息

• Synthesis of orthogonally protected 1,2-diaminopropanoic acids by ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine: a study of the regioselectivity of the reaction
  作者：Keith O’Brien、Fintan Kelleher

  DOI：10.1016/j.tetlet.2013.09.116

  日期：2013.11

  Orthogonally protected 1,2-diaminopropanoic acids (DAPs) have been synthesised in good yields by the ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine. The choice of both the N-activating group and ester alkyl group had a significant influence on the ratio of attack at the α or β positions of the aziridine. However, the regiochemical outcome is not predictable

  通过3-未取代的N-活化的N-活化的氮丙啶2-羧酸酯与对-甲氧基苄胺的开环，以高收率合成了正交保护的1,2-二氨基丙酸（DAP）。N-活化基团和酯烷基的选择对氮丙啶的α或β位置的进攻比率具有显着影响。但是，区域化学结果是不可预测的。
• Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates
  作者：Keith O’Brien、Keith ó Proinsias、Fintan Kelleher

  DOI：10.1016/j.tetlet.2013.02.096

  日期：2013.5

  Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or beta-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs). The required DAPs were also synthesised by ring-opening of N-protected aziridine 2-carboxylates with para-methoxybenzylamine. (C) 2013 Elsevier Ltd. All rights reserved.