(R)-2-tert-butoxycarbonylamino-4-(diethoxyphosphoryl)butyric acid | 890301-79-8

• 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: (R)-2-tert-butoxycarbonylamino-4-(diethoxyphosphoryl)butyric acid
• 英文别名: 2-((tert-butoxycarbonyl)amino)-4-(diethoxyphosphoryl)butanoic acid；Butanoic acid,4-(diethoxyphosphinyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-,(2r)-；(2R)-4-diethoxyphosphoryl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 890301-79-8
• 化学式: C₁₃H₂₆NO₇P
• 分子量: 339.326
• InChiKey: ZELUYLMMIUIKQS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-butoxycarbonylamino-4-(diethoxyphosphoryl)butyric acid 在 三氟乙酸 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以100%的产率得到1-carboxy-3-(diethoxyphosphoryl)propan-1-aminium chloride
  参考文献：
  名称：

  新型易于循环利用的双功能携带三肽的磷酸，可用于醛与硝基烯烃的立体选择性迈克尔加成反应

  摘要：

  首次将结合了氨基催化和膦酸活化的新型双功能有机催化剂库作为有效的工具，用于醛与几种芳香族硝基烯烃的立体选择性迈克尔加成反应，选择性高达95：5 dr和93：7 er。由于它们的高水溶性，这些催化剂易于回收利用，并且可以在多个循环中重复使用，而没有任何明显的选择性损失。

  DOI：

  10.1002/adsc.201500794
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 碘苯二乙酸 、 三氟化硼乙醚 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 81.75h， 生成 (R)-2-tert-butoxycarbonylamino-4-(diethoxyphosphoryl)butyric acid
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060

文献信息

• Novel Easily Recyclable Bifunctional Phosphonic Acid Carrying Tripeptides for the Stereoselective Michael Addition of Aldehydes with Nitroalkenes
  作者：Margery Cortes-Clerget、Olivier Gager、Maelle Monteil、Jean-Luc Pirat、Evelyne Migianu-Griffoni、Julia Deschamp、Marc Lecouvey

  DOI：10.1002/adsc.201500794

  日期：2016.1.7

  A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation was used for the first time as an efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes with good selectivities up to 95:5 dr and 93:7 er. Due to their high water solubility, the catalysts were easily recyclable and could be reused over several cycles

  首次将结合了氨基催化和膦酸活化的新型双功能有机催化剂库作为有效的工具，用于醛与几种芳香族硝基烯烃的立体选择性迈克尔加成反应，选择性高达95：5 dr和93：7 er。由于它们的高水溶性，这些催化剂易于回收利用，并且可以在多个循环中重复使用，而没有任何明显的选择性损失。
• Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists
  作者：Frank W. Foss、Ashley H. Snyder、Michael D. Davis、Michael Rouse、Mark D. Okusa、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/j.bmc.2006.10.060

  日期：2007.1

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.