diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate | 948832-20-0

• 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 (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate
• 英文别名: [(3R,5R)-3-diethoxyphosphoryl-2-[(1S)-1-phenylethyl]-1,2-oxazolidin-5-yl]methanol
• CAS: 948832-20-0
• 化学式: C₁₆H₂₆NO₅P
• 分子量: 343.36
• InChiKey: HTPSMBGVVOBYJV-NUEKZKHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate 在 sodium periodate 、 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  (1-氨基-3-羟基丙烷-1,3-二基)二膦酸的四种对映体作为4-羟基谷氨酸二膦酸酯类似物的合成

  摘要：

  获得了新设计的4-羟基谷氨酸膦酸酯类似物(1-氨基-3-羟基丙烷-1,3-二基)二膦酸的所有对映体。合成策略包括( R )-和( S )-1-( N -Boc-氨基)-3-氧代丙基膦酸二乙酯与亚磷酸二乙酯的Abramov反应，分离非对映异构体[1-( N -Boc-氨基)-3-羟基丙烷-1,3-二基]二膦酸酯作为O-保护的酯，然后水解成对映体膦酸。通过比较从相应的顺式和反式-[1-( N -Boc-氨基)-3对获得的( S ) -O-甲基扁桃酸酯的31 P NMR化学位移，确定了对映体膦酸酯的绝对构型。 -羟基丙烷-1,3-二基]二膦酸盐根据溢出规则。

  DOI：

  10.3390/molecules27092699
• 作为产物：
  描述：

  N-[(S)-1-phenylethyl]-C-(diethoxyphosphoryl)nitrone 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 、 zinc(II) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 244.0h， 生成 diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate
  参考文献：
  名称：

  Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines

  摘要：

  All the enantiomers of 0,0-diethyl 4-hydroxypyrrolidinyl-2-phosphonates, phosphonate analogues of cis- and trans-4hydroxyprolines, have been obtained for the first time. The synthetic strategy involved 1,3-dipolar cycloaddition of (R)- and (S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrones to ally] alcohol and separation of the corresponding 0,0-diethyl 5-(hydroxymethyl)-2-(1-phenylethyl)isoxazolidinyl-3-phosphonates, which were subsequently mesylated and hydrogenated to undergo intramolecular cyclisation. Absolute configurations of the enantiomeric proline phosphonates were established after N- and 0-derivatization with (S)-O-methylmandelic acid employing the Trost model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.006

文献信息

• Enantioselective synthesis of phosphonate analogues of (R)- and (S)-homoserine
  作者：Dorota G. Piotrowska、Iwona E. Głowacka

  DOI：10.1016/j.tetasy.2007.11.007

  日期：2007.11

  The enantioselective synthesis of (R)- and (S)-1-amino-3-hydroxypropylphosphonic acid, the phosphonate analogues of (S)and (R)-homoserine, has been accomplished in four steps and good overall yield starting from diethyl (3R,5R)- or (3S,5S)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate, respectively. (c) 2007 Elsevier Ltd. All rights reserved.
• Enantiomerically pure phosphonate analogues of cis- and trans-4-hydroxyprolines
  作者：Dorota G. Piotrowska、Iwona E. Głowacka

  DOI：10.1016/j.tetasy.2007.06.006

  日期：2007.6

  All the enantiomers of 0,0-diethyl 4-hydroxypyrrolidinyl-2-phosphonates, phosphonate analogues of cis- and trans-4hydroxyprolines, have been obtained for the first time. The synthetic strategy involved 1,3-dipolar cycloaddition of (R)- and (S)-N-(1-phenylethyl)-C-(diethoxyphosphoryl)nitrones to ally] alcohol and separation of the corresponding 0,0-diethyl 5-(hydroxymethyl)-2-(1-phenylethyl)isoxazolidinyl-3-phosphonates, which were subsequently mesylated and hydrogenated to undergo intramolecular cyclisation. Absolute configurations of the enantiomeric proline phosphonates were established after N- and 0-derivatization with (S)-O-methylmandelic acid employing the Trost model. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Four Enantiomers of (1-Amino-3-Hydroxypropane-1,3-Diyl)Diphosphonic Acid as Diphosphonate Analogues of 4-Hydroxyglutamic Acid
  作者：Liwia Lebelt、Iwona E. Głowacka、Dorota G. Piotrowska

  DOI：10.3390/molecules27092699

  日期：——

  All the enantiomers of (1-amino-3-hydroxypropane-1,3-diyl)diphosphonic acid, newly design phosphonate analogues of 4-hydroxyglutamic acids, were obtained. The synthetic strategy involved Abramov reactions of diethyl (R)- and (S)-1-(N-Boc-amino)-3-oxopropylphosphonates with diethyl phosphite, separation of diastereoisomeric [1-(N-Boc-amino)-3-hydroxypropane-1,3-diyl]diphosphonates as O-protected esters

  获得了新设计的4-羟基谷氨酸膦酸酯类似物(1-氨基-3-羟基丙烷-1,3-二基)二膦酸的所有对映体。合成策略包括( R )-和( S )-1-( N -Boc-氨基)-3-氧代丙基膦酸二乙酯与亚磷酸二乙酯的Abramov反应，分离非对映异构体[1-( N -Boc-氨基)-3-羟基丙烷-1,3-二基]二膦酸酯作为O-保护的酯，然后水解成对映体膦酸。通过比较从相应的顺式和反式-[1-( N -Boc-氨基)-3对获得的( S ) -O-甲基扁桃酸酯的31 P NMR化学位移，确定了对映体膦酸酯的绝对构型。 -羟基丙烷-1,3-二基]二膦酸盐根据溢出规则。