((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid dimethyl ester | 107133-10-8

• 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 dimethyl ester
• 英文别名: (R)-benzyl N-[1-(dimethoxyphosphoryl)-2-phenylethyl]carbamate
• CAS: 107133-10-8
• 化学式: C₁₈H₂₂NO₅P
• 分子量: 363.35
• InChiKey: CPPBAYILCGKGHR-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid dimethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以82%的产率得到methyl hydrogen <<1(R)-1-N-<(phenylmethoxy)carbonyl>amino>-2-phenylethyl>phosphonate
  参考文献：
  名称：

  Synthesis of five enantiomerically pure haptens designed for in vitro evolution of antibodies with peptidase activity

  摘要：

  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

  DOI：

  10.1016/0968-0896(96)00085-5
• 作为产物：
  描述：

  在 盐酸 、 溴 作用下， 以 甲醇 、 水 为溶剂， 反应 2.75h， 生成 ((R)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of H-Phosphinic Acids Bearing Natural Amino Acid Residues

  摘要：

  The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butane-sulfinyl imines. Good yields and moderate to high enantiose-lectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the alpha-aminophosphinates to oligopetides were reported.

  DOI：

  10.1021/jo400798f

文献信息

• The Synthesis of α-Aminophosphonates via Enantioselective Organocatalytic Reaction of 1-(N-Acylamino)alkylphosphonium Salts with Dimethyl Phosphite
  作者：Alicja Walęcka-Kurczyk、Krzysztof Walczak、Anna Kuźnik、Sebastian Stecko、Agnieszka Październiok-Holewa

  DOI：10.3390/molecules25020405

  日期：——

  an effective method for this type of transformation using a racemic mixture of starting N-protected α-amino acids and a chiral catalyst. Herein, a simple and efficient stereoselective organocatalytic α-amidoalkylation of dimethyl phosphite by 1-(N-acylamino)alkyltriphenylphosphonium salts to enantiomerically enriched α-aminophosphonates is reported. Using 5 mol% of chiral quinine- or hydroquinine-derived

  α-氨基膦酸是α-氨基酸的磷类似物。由于其独特的生物活性，这种类型的化合物在医学和作物保护中有着广泛的应用。这些活动中的一个关键因素是立体异构体的构型。迄今为止，只有少数将 α-氨基酸立体选择性地转化为磷类似物的方法是已知的，而且所有方法都基于不对称诱导，因此涉及手性底物的使用。相比之下，我们专注于开发一种使用起始 N-保护的 α-氨基酸和手性催化剂的外消旋混合物进行此类转化的有效方法。在此处，报道了通过 1-（N-酰基氨基）烷基三苯基鏻盐对亚磷酸二甲酯进行简单有效的立体选择性有机催化 α-酰胺烷基化反应生成对映体富集的 α-氨基膦酸酯。使用 5 mol% 的手性奎宁或氢奎宁衍生的季铵盐，最终产品的产率高达 98%，ee 高达 92%。起始鏻盐很容易从α-氨基酸衍生物通过脱羧甲氧基化和随后用三苯基鏻四氟硼酸盐取代获得。通过非手性快速色谱对选定的 α-氨基膦酸酯衍生物进行适当的对映体自歧化 (SDE)
• Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation
  作者：Mark J. Burk、Timothy A. Stammers、Judith A. Straub

  DOI：10.1021/ol9906099

  日期：1999.8.1

  [GRAPHICS]Cationic rhodium catalysts of the C-2 symmetric DuPHOS (1) and BPE (2) ligands have demonstrated the ability to asymmetrically hydrogenate a novel series of enol phosphonates (3) in good to excellent enantiomeric excess under mild conditions. Initial studies toward the catalytic asymmetric hydrogenation of enamido phosphonates (6 and 7) using the DuPHOS-Rh+ catalysts are also reported.