diethyl (1R)-1-{[carbobenzyloxy]amino}ethylphosphonate | 98857-08-0

• 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: diethyl (1R)-1-{[carbobenzyloxy]amino}ethylphosphonate
• 英文别名: (R)-diethyl 1-benzyloxycarbonylaminoethanephosphonate；diethyl N-carbobenzoxy-L-1-aminoethylphosphonate；benzyl N-[(1R)-1-diethoxyphosphorylethyl]carbamate
• CAS: 98857-08-0
• 化学式: C₁₄H₂₂NO₅P
• 分子量: 315.306
• InChiKey: WYBRLTMWSUYZGY-GFCCVEGCSA-N

物化性质

• 沸点：
  446.1±38.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (1R)-1-{[carbobenzyloxy]amino}ethylphosphonate 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以73.5%的产率得到(R)-(1-Aminoethyl)phosphonsaeure-diethylester
  参考文献：
  名称：

  [EN] THERAPEUTICALLY USEFUL ANTIBACTERIAL COMPOUNDS
  [FR] COMPOSES ANTIBACTERIENS A USAGE THERAPEUTIQUE

  摘要：

  本文揭示了一种化合物，在哺乳动物体内，特别是在人体中具有抗生素活性，该化合物包括一个与细菌杀菌或细菌抑制毒性部分相连的摄取基团，所述摄取基团促进细菌摄取该化合物，该毒性部分对细菌产生细菌杀菌或细菌抑制作用，其中：(a) 该化合物对哺乳动物体不具有毒性；(b) 摄取基团与毒性部分之间的连接是一种可被细菌产生的酶或酶裂解的连接，但不容易被主体产生的酶裂解，且在接触细菌之前暴露于主体的化合物；(c) 当毒性部分从摄取基团中裂解时，对细菌具有毒性，但对主体不具有毒性。

  公开号：

  WO2005067939A1
• 作为产物：
  描述：

  1-氨基乙基膦酸二乙酯 在 Candida antarctica lipase B 、 碳酸氢钠 作用下， 以 异丙醚 、 水 为溶剂， 反应 123.0h， 生成 diethyl (1R)-1-{[carbobenzyloxy]amino}ethylphosphonate
  参考文献：
  名称：

  Enzymatic synthesis of optically active 1- and 2-aminoalkanephosphonates

  摘要：

  A number of 1- and 2-aminoalkanephosphonates were resolved with high enantioselectivity by Candida antarctica lipase B-catalyzed acetylation. By this method, optically pure aminoalkanephosphonates and amidoalkanephosphonates, the precursors of the corresponding aminoalkanephosphonic acids, were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00995-5

文献信息

• Optically active diethyl N-(p-toluenesulfonyl)-aziridine 2-phosphonates as chiral synthons for the synthesis of β-substituted α-amino phosphonates
  作者：E. Kurt Dolence、Jason B. Roylance

  DOI：10.1016/j.tetasy.2004.08.034

  日期：2004.10

  versatile approach for the synthesis of both protected enantiomers of aziridine 2-phosphonates for use as chiral synthons has been developed. The aziridines arise from either (R)- or (S)-phosphonoserine diethyl esters followed by N-tosylation, O-mesylation and cyclization with sodium hydride. These highly enantio-enriched aziridine 2-phosphonates have been shown to react with carbon, nitrogen, sulfur

  已经开发了一种通用的方法，用于合成用作手性合成子的两种保护的氮丙啶氮丙啶的两种对映体。氮丙啶衍生自（R）-或（S）-膦丝氨酸二乙酯，接着是N-甲苯磺酸化，O-甲磺酰化和用氢化钠环化。这些高度对映体富集的氮丙啶2-膦酸酯可与碳，氮，硫，氢化物，氟化物和磷亲核试剂反应，从而可在（R）中快速生成各种β-取代的α-氨基膦酸酯。-或（S）-配置。如果是巯基亲核试剂，则使用化学计量的Tri- n-丁基膦对于清洁生产相应的硫化物产品是必需的。利用手性HPLC方法监测合成过程，以评估可能得到的产物的对映体过量。
• Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
  作者：Frank R. Atherton、Cedric H. Hassall、Robert W. Lambert

  DOI：10.1021/jm00151a005

  日期：1986.1

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.