diethyl (1R,2S)-1-chloro-3-methyl-2-hydroxybutylphosphonate | 1245930-53-3

• 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: diethyl (1R,2S)-1-chloro-3-methyl-2-hydroxybutylphosphonate
• 英文别名: (1R,2S)-1-chloro-1-diethoxyphosphoryl-3-methylbutan-2-ol
• CAS: 1245930-53-3
• 化学式: C₉H₂₀ClO₄P
• 分子量: 258.682
• InChiKey: VERSZDADBYKASW-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1R,2S)-1-chloro-3-methyl-2-hydroxybutylphosphonate 、 2-过氧乙酰丙酰氯 在 吡啶 作用下， 生成 (1R,2S)-1-chloro-1-(diethoxyphosphoryl)-3-methylbutan-2-yl (S)-2-acetoxypropanoate
  参考文献：
  名称：

  Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation

  摘要：

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.017
• 作为产物：
  描述：

  diethyl 1-chloro-3-methyl-2-oxobutylphosphonate 在 [{RuCl((S)-MeO-BIPHEP)}2(μ-Cl)3][NH2Me2] 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、7.0 MPa 条件下， 反应 100.0h， 以8%的产率得到1-Diethoxyphosphoryl-3-methylbutan-2-ol
  参考文献：
  名称：

  Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation

  摘要：

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.017

文献信息

• Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation
  作者：Sébastien Prévost、Sébastien Gauthier、Maria Cristina Caño de Andrade、Céline Mordant、Ali Rhida Touati、Philippe Lesot、Philippe Savignac、Tahar Ayad、Phannarath Phansavath、Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/j.tetasy.2010.05.017

  日期：2010.6

  The dynamic kinetic resolution (DKR) of racemic alpha-chloro beta-ketoesters and alpha-chloro beta-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding alpha-chloro beta-hydroxyesters and alpha-chloro beta-hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere (R) which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, C-13 NMR in chiral oriented solvents was used to investigate the DKR effect. (C) 2010 Elsevier Ltd. All rights reserved.