(S)-diethyl 2-hydroxybutylphosphonate | 451503-59-6

• 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: (S)-diethyl 2-hydroxybutylphosphonate
• 英文别名: diethyl (S)-2-hydroxybutylphosphonate；diethyl 2-hydroxybutylphosphonate；(2S)-1-diethoxyphosphorylbutan-2-ol
• CAS: 451503-59-6
• 化学式: C₈H₁₉O₄P
• 分子量: 210.21
• InChiKey: HHDWGFBRTJYZKM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 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：

  甲氧基-三氟甲基苯 、 (S)-diethyl 2-hydroxybutylphosphonate 在 N,N-二甲基-1,3-二氨基丙烷 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 72.08h， 生成 (S)-1-(diethoxyphosphoryl)butan-2-yl (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Application of cyanobacteria for chiral phosphonate synthesis

  摘要：

  这是一份关于形态上不同的蓝藻菌株的首次报告：阿尔特罗螺旋藻（Arthrospira maxima）、拟氮球藻（Nostoc cf-muscorum）和球形小结藻（Nodularia sphaerocarpa），它们用于选择性、结构不同的二乙基氧膦酸酯的对映选择性生物还原。非对称氢转移的效率在很大程度上依赖于底物的化学结构。阿尔特罗螺旋藻仅对二乙基(S)-2-氧丙基膦酸酯表现出活性（产率20%，对映体过量99%），而采用拟氮球藻作为生物催化剂能够得到具有高对映选择过量（99%）和26%转化率的二乙基(S)-2-羟基-2-苯乙基膦酸酯。使用球形小结藻的结果最为显著——可获得转化率为99%且光学纯度为92%的二乙基(S)-2-羟基-2-苯乙基膦酸酯。首次实现了带有芳香侧基的氧膦酸酯在羰基功能团附近的对映选择性生物转化。此外，流式细胞术显示球形小结藻细胞对所测定的外源物质——2-氧-2-苯乙基膦酸酯具有极好的耐受性，这些细胞在10 mM的生物转化底物浓度下仍保持活力，而之前针对真菌生物催化剂仅为1 mM。研究还考察了培养基、光源和光周期（光：暗）对生物转化过程有效性的影响。

  DOI：

  10.1039/c5gc01195g
• 作为产物：
  描述：

  (S)-(+)-diethyl 2-benzyloxybutylphosphonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、374.93 kPa 条件下， 反应 2.5h， 以89%的产率得到(S)-diethyl 2-hydroxybutylphosphonate
  参考文献：
  名称：

  On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae

  摘要：

  2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 mu g/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%)in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.012

文献信息

• Kinetic resolution of hydroxyalkanephosphonates catalyzed by Candida antarctica lipase B in organic media
  作者：Yonghui Zhang、Chengye Yuan、Zuyi Li

  DOI：10.1016/s0040-4020(02)00229-6

  日期：2002.4

  A series of hydroxyalkanephosphonates were studied as substrates for CALB catalyzed acetylation with emphasis on enantioselectivity and chemical structure of substrates. Some hydroxyalkanephosphonates could be resolved successfully to give both (R)- and (S)-isomers with high enantiomeric excess.

  研究了一系列羟基链烷膦酸酯作为CALB催化乙酰化反应的底物，重点是底物的对映选择性和化学结构。一些羟基链烷膦酸酯可以成功地拆分，以得到具有高对映体过量的（R）-和（S）-异构体。
• Application of cyanobacteria for chiral phosphonate synthesis
  作者：M. Górak、E. Żymańczyk-Duda

  DOI：10.1039/c5gc01195g

  日期：——

  This is the first report on morphologically different strains of cyanobacteria: Arthrospira maxima, Nostoc cf-muscorum and Nodularia sphaerocarpa used for enantioselective bioreduction of selected, structurally different diethyl esters of oxophosphonic acids. The efficiency of the asymmetric hydrogen transfer was strongly dependent on the chemical structure of the substrates. Arthrospira maxima was active only toward diethyl (S)-2-oxopropylphosphonate (20% of yield, 99% of ee), whereas the application of Nostoc cf-muscorum as a biocatalyst allowed diethyl (S)-2-hydroxy-2-phenylethylphosphonate with a high enantiomeric excess (99%) and with 26% conversion degree to be obtained. Employing Nodularia sphaerocarpa led to the most spectacular result – diethyl (S)-2-hydroxy-2-phenylethylphosphonate with a degree of conversion of 99% and an optical purity of 92%. Enantioselective bioconversion of oxophosphonate with an aromatic side group located in the immediate vicinity of the carbonyl functionality was achieved for the first time. Additionally, flow cytometry showed excellent resistance of the cells of Nodularia sphaerocarpa against the examined xenobiotic – 2-oxo-2-phenylethylphosphonate, these cells remain viable at the concentration of 10 mM of the bioconversion substrate compared to the 1 mM described previously for a fungal biocatalyst. The effect of cultivation medium, light source and light cycle (light : dark) on the effectiveness of the biotransformation process was examined.

  这是一份关于形态上不同的蓝藻菌株的首次报告：阿尔特罗螺旋藻（Arthrospira maxima）、拟氮球藻（Nostoc cf-muscorum）和球形小结藻（Nodularia sphaerocarpa），它们用于选择性、结构不同的二乙基氧膦酸酯的对映选择性生物还原。非对称氢转移的效率在很大程度上依赖于底物的化学结构。阿尔特罗螺旋藻仅对二乙基(S)-2-氧丙基膦酸酯表现出活性（产率20%，对映体过量99%），而采用拟氮球藻作为生物催化剂能够得到具有高对映选择过量（99%）和26%转化率的二乙基(S)-2-羟基-2-苯乙基膦酸酯。使用球形小结藻的结果最为显著——可获得转化率为99%且光学纯度为92%的二乙基(S)-2-羟基-2-苯乙基膦酸酯。首次实现了带有芳香侧基的氧膦酸酯在羰基功能团附近的对映选择性生物转化。此外，流式细胞术显示球形小结藻细胞对所测定的外源物质——2-氧-2-苯乙基膦酸酯具有极好的耐受性，这些细胞在10 mM的生物转化底物浓度下仍保持活力，而之前针对真菌生物催化剂仅为1 mM。研究还考察了培养基、光源和光周期（光：暗）对生物转化过程有效性的影响。
• On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae
  作者：Anna Schweifer、Friedrich Hammerschmidt

  DOI：10.1016/j.bmcl.2007.12.012

  日期：2008.5

  2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 mu g/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%)in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin. (c) 2008 Elsevier Ltd. All rights reserved.