(R)-4-[2-(diethoxyphosphoryl)vinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (R)-4-[2-(diethoxyphosphoryl)vinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(2-(diethoxyphosphoryl)vinyl)-2,2-dimethyloxazolidine-3-carboxylate；3-Oxazolidinecarboxylic acid, 4-[2-(diethoxyphosphinyl)ethenyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R)-；tert-butyl (4R)-4-[(E)-2-diethoxyphosphorylethenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 化学式: C₁₆H₃₀NO₆P
• 分子量: 363.391
• InChiKey: BZQGFBWFTYUOHN-OCHBPSSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-[2-(diethoxyphosphoryl)vinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 87.0h， 生成 [(R)-3-tert-Butoxycarbonylamino-3-(4-decyl-phenylcarbamoyl)-propyl]-phosphonic acid diethyl ester
  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
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 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 、 丙酮 为溶剂， 反应 6.75h， 生成 (R)-4-[2-(diethoxyphosphoryl)vinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester
  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。
• [EN] PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PHOSPHORIBOSYLTRANSFÉRASES ET LEURS UTILISATIONS
  申请人：IND RES LTD

  公开号：WO2012150866A1

  公开（公告）日：2012-11-08

  The invention relates to compounds of formula (I) that are inhibitors of hypoxanthine and/or guanine purine phosphoribosyltransferases and to pharmaceutical compositions containing the compounds, processes for preparing the compounds, and methods of treating diseases or conditions in which it is desirable to inhibit hypoxanthine and/or guanine purine phosphoribosyltransferases. Such diseases include malaria.

  这项发明涉及到式（I）的化合物，这些化合物是次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的抑制剂，以及含有这些化合物的药物组合物、制备这些化合物的方法，以及治疗希望抑制次黄嘌呤和/或鸟嘌呤磷酸核糖转移酶的疾病或症状的方法。这些疾病包括疟疾。
• 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.