methyl 2-(methoxy(methyl)phosphoryloxy)-(2S)-phenylacetate

• 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: methyl 2-(methoxy(methyl)phosphoryloxy)-(2S)-phenylacetate
• 英文别名: methyl (2S)-2-[methoxy(methyl)phosphoryl]oxy-2-phenylacetate
• 化学式: C₁₁H₁₅O₅P
• 分子量: 258.211
• InChiKey: IBUMDMIRKNDCPY-YOZOHBORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基氯膦酸甲酯 、 L-扁桃酸甲酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以63%的产率得到methyl 2-(methoxy(methyl)phosphoryloxy)-(2S)-phenylacetate
  参考文献：
  名称：

  Synthesis of both RP and SP enantiomers of unsymmetrical methylphosphonates based on a new approach utilizing a P-ester bond with α-hydroxyacids

  摘要：

  Condensation of methyl methylphosphonochloridate with the dilithium salt of 2-methyllactic acid gave P-racemic methylphosphonates which unexpectedly contained two units of alpha-hydroxyacid linked via carboxylic ester bond. The racemic mixture was chromatographically separated via diastereomeric salts with quinine or cinchonine to give, based on the X-ray analysis, pure (R-p)-(+) and (S-p)-(-) enantiomers. Both enantiomers were immobilized on the ArgoGel (R)-OH solid support. Condensation of methyl methylphosphonochloridate with alpha-hydroxyacid methyl esters [2-methyllactate, (S-C)-(-)-lactate, methyl (S-C)-(+) and (R-C)(-)-mandelates] gave chromatographically inseparable 1:1 mixtures of diastereomers in 63-69% yields. A basic hydrolysis of the latter resulted in a selective and unexpected cleavage of the P-OMe group in a quantitative yield [(S-C)-(+) and (R-C)-(-)-mandelates, (S-C) -(-)-lactate] or simultaneous cleavages of P-OMe and C(O)OMe groups (2-methyllactate). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.015

文献信息

• Synthesis of both RP and SP enantiomers of unsymmetrical methylphosphonates based on a new approach utilizing a P-ester bond with α-hydroxyacids
  作者：Piotr Bałczewski、Aldona Szadowiak、Tomasz Białas、Wanda M. Wieczorek、Agnieszka Balińska

  DOI：10.1016/j.tetasy.2006.04.015

  日期：2006.4

  Condensation of methyl methylphosphonochloridate with the dilithium salt of 2-methyllactic acid gave P-racemic methylphosphonates which unexpectedly contained two units of alpha-hydroxyacid linked via carboxylic ester bond. The racemic mixture was chromatographically separated via diastereomeric salts with quinine or cinchonine to give, based on the X-ray analysis, pure (R-p)-(+) and (S-p)-(-) enantiomers. Both enantiomers were immobilized on the ArgoGel (R)-OH solid support. Condensation of methyl methylphosphonochloridate with alpha-hydroxyacid methyl esters [2-methyllactate, (S-C)-(-)-lactate, methyl (S-C)-(+) and (R-C)(-)-mandelates] gave chromatographically inseparable 1:1 mixtures of diastereomers in 63-69% yields. A basic hydrolysis of the latter resulted in a selective and unexpected cleavage of the P-OMe group in a quantitative yield [(S-C)-(+) and (R-C)-(-)-mandelates, (S-C) -(-)-lactate] or simultaneous cleavages of P-OMe and C(O)OMe groups (2-methyllactate). (c) 2006 Elsevier Ltd. All rights reserved.