((R)-Amino-phenyl-methyl)-phosphonic acid diallyl ester | 614754-53-9

• 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)-Amino-phenyl-methyl)-phosphonic acid diallyl ester
• 英文别名: (R)-bis(prop-2-enoxy)phosphoryl-phenylmethanamine
• CAS: 614754-53-9
• 化学式: C₁₃H₁₈NO₃P
• 分子量: 267.265
• InChiKey: RAOOEOYYCAGEFW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((R)-Amino-phenyl-methyl)-phosphonic acid diallyl ester 在 四丁基氟化铵 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of phosphoramidate α(2-6)Sialyltransferase transition-State analogue inhibitors

  摘要：

  The asymmetric synthesis of novel, potent phosphoramidate alpha(2-6)sialyltransferase transition-state analogue inhibitors such as (R)-9 (K-i - 68 muM) is described, via condensation of cytidine phosphitamide 6 with key chiral, non-racemic alpha-aminophosphonates, prepared in > 98 % ee by Mitsunobu azidation followed by Staudinger reduction of the corresponding chiral, non-racemic alpha-hydroxyphosphonates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00672-3
• 作为产物：
  描述：

  二(丙-2-烯氧基)磷酰基甲基苯 在 三(2-氯乙基)胺 、 水 、 sodium hexamethyldisilazane 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 30.33h， 生成 ((R)-Amino-phenyl-methyl)-phosphonic acid diallyl ester
  参考文献：
  名称：

  Stereoselective synthesis of phosphoramidate α(2-6)Sialyltransferase transition-State analogue inhibitors

  摘要：

  The asymmetric synthesis of novel, potent phosphoramidate alpha(2-6)sialyltransferase transition-state analogue inhibitors such as (R)-9 (K-i - 68 muM) is described, via condensation of cytidine phosphitamide 6 with key chiral, non-racemic alpha-aminophosphonates, prepared in > 98 % ee by Mitsunobu azidation followed by Staudinger reduction of the corresponding chiral, non-racemic alpha-hydroxyphosphonates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00672-3

文献信息

• Stereoselective synthesis of phosphoramidate α(2-6)Sialyltransferase transition-State analogue inhibitors
  作者：Danielle Skropeta、Ralf Schwörer、Richard R. Schmidt

  DOI：10.1016/s0960-894x(03)00672-3

  日期：2003.10

  The asymmetric synthesis of novel, potent phosphoramidate alpha(2-6)sialyltransferase transition-state analogue inhibitors such as (R)-9 (K-i - 68 muM) is described, via condensation of cytidine phosphitamide 6 with key chiral, non-racemic alpha-aminophosphonates, prepared in > 98 % ee by Mitsunobu azidation followed by Staudinger reduction of the corresponding chiral, non-racemic alpha-hydroxyphosphonates. (C) 2003 Elsevier Ltd. All rights reserved.