((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid | 107072-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid
• 英文别名: [(1R)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphonic acid
• CAS: 107072-62-8
• 化学式: C₁₆H₁₈NO₅P
• 分子量: 335.296
• InChiKey: VSULGWZITIYPLP-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid 在 氢溴酸 作用下， 以 水 为溶剂， 生成 L-Phenylalanine phosphonate
  参考文献：
  名称：

  Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

  摘要：

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00297-1
• 作为产物：
  描述：

  ((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid 在 sodium periodate 作用下， 生成 ((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid
  参考文献：
  名称：

  Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

  摘要：

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00297-1

文献信息

• A straightforward synthesis of α-amino phosphonate monoesters using BroP or TPyClU
  作者：Nathalie Galéotti、Jacques Coste、Philippe Bedos、Patrick Jouin

  DOI：10.1016/0040-4039(96)00742-3

  日期：1996.6

  Monoesters of N-protected α-amino phosphonic acid were prepared from phosphonic acid using BroP or TPyClU as activating agent. This reaction proceeds with good yield, even with hindered alcohols.

  使用BroP或TPyClU作为活化剂，由膦酸制备N-保护的α-氨基膦酸的单酯。即使受阻醇，该反应也以良好的收率进行。
• Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity
  作者：Jürgen Wagner、Richard A. Lerner、Carlos F. Barbas

  DOI：10.1016/0968-0896(96)00085-5

  日期：1996.6

  A series of five haptens have been synthesized for use in in vitro selection experiments from combinatorial antibody libraries. Haptens were designed for the recruitment of serine and cysteine protease reaction mechanisms for the cleavage of Phe-Ala and Phe-Phe (L,L) dipeptide analogues. For the selection of transition state stabilization, Phe(P)(O)Ala (7) and PheP(O)Phe (10) derivatives were synthesized using the Mitsunobu approach where Phe(P) represents the phosphonic acid analogue of phenylalanine and (O)Phe and (O)Ala represent (L)-beta-phenyllactic and (L)-lactic acid, respectively. Optically pure peptidyl diazomethyl ketones 16 and 22 were synthesized for selection of the catalytic ensemble of cysteine proteases. An optically pure dipeptidyl boronic acid 26 was synthesized for the selection of the catalytic ensemble of serine proteases. A strategy for the evolution of catalytic antibodies using these haptens was developed which includes mechanism-based selections. Since mechanism based selections result in covalent trapping of species from libraries, diol and disulfide containing haptenic linkers were developed for the oxidative or reductive release of selected catalysts. Copyright 1O 1996 Elsevier Science Ltd
• PROCÉDÉS DE PRÉPARATION D'ACIDES ALPHA- ET BÉTA- AMINOPHOSPHORÉS ET LEURS DÉRIVÉS
  申请人：Diverchim

  公开号：EP2723701A1

  公开（公告）日：2014-04-30
• [EN] PROCESSES FOR PREPARING PHOSPHORUS-CONTAINING ?- AND ?-AMINO ACIDS AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉS DE PRÉPARATION D'ACIDES a- ET ß-AMINOPHOSPHORÉS ET LEURS DÉRIVÉS
  申请人：DIVERCHIM

  公开号：WO2012175837A1

  公开（公告）日：2012-12-27

  L'invention a pour objet l'utilisation d'un composé organométallique pour la mise en œuvre d'un procédé de préparation de dérivés chiraux constitués d'α- ou β-aminophosphoacides ainsi que leurs dérivés avec des excès énantiomériques d'au moins 50%, par réaction d'un produit de départ constitué d'un a- ou β- déhydroaminophosphoester avec un composé organométallique, en présence d'un catalyseur contenant un métal de transition et un ligand chiral, à une température variant de -20°C à 90°C.
• Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11
  作者：Brian A. McKittrick、Andrew W. Stamford、Xiaoyu Weng、Ke Ma、Samuel Chackalamannil、Michael Czarniecki、ReneéM. Cleven、Ahmad B. Fawzi

  DOI：10.1016/0960-894x(96)00297-1

  日期：1996.7

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd