diallyl (R)-α-hydroxy(m-phenoxy)benzylphosphonate | 536739-09-0

• 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: diallyl (R)-α-hydroxy(m-phenoxy)benzylphosphonate
• CAS: 536739-09-0
• 化学式: C₁₉H₂₁O₅P
• 分子量: 360.346
• InChiKey: ZOHINQZQAFKLNP-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diallyl (R)-α-hydroxy(m-phenoxy)benzylphosphonate 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 20.0h， 生成 [(S)-Azido-(3-phenoxy-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
• 作为产物：
  描述：

  diallyl m-phenoxybenzylphosphonate 在 sodium hexamethyldisilazane 、 (1R)-(−)-(10-camphorsulfonyl)oxaziridine 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 diallyl (R)-α-hydroxy(m-phenoxy)benzylphosphonate
  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

• Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates
  作者：Danielle Skropeta、Richard R. Schmidt

  DOI：10.1016/s0957-4166(02)00786-3

  日期：2003.1

  Chiral, non-racemic alpha-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the alpha-hydroxyphosphonates was established from H-1 and P-31 NMR spectroscopy of the (S)-O-methylmandelate esters. Deprotection of the diallyl alpha-hydroxyphosphonates under neutral conditions furnished the corresponding free phosphonic acids, retaining a high degree of stereochemical purity (90 to >98% ee). (C) 2003 Elsevier Science Ltd. All rights reserved.