(+)-(2R)-2-hydroxy-3-(N,N,N-trimethylammonium)propylphosphonic acid

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+)-(2R)-2-hydroxy-3-(N,N,N-trimethylammonium)propylphosphonic acid
• 英文别名: (R)-(+)-2-hydroxy-3-(N,N,N-trimethylammonium)phosphonic acid；(R)-[2-hydroxy-3-(trimethylammonio)propyl]phosphonic acid；(+)-(R)-phospho-carnitine；(R)-(+)-phosphocarnitine；(R)-phosphocarnitine；hydroxy-[(2R)-2-hydroxy-3-(trimethylazaniumyl)propyl]phosphinate
• 化学式: C₆H₁₆NO₄P
• 分子量: 197.171
• InChiKey: CFKIUJQHVVMWGR-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(3-chloro-2-hydroxypropyl)phosphonic acid 、 三甲胺 以 水 为溶剂， 反应 48.0h， 以80%的产率得到(+)-(2R)-2-hydroxy-3-(N,N,N-trimethylammonium)propylphosphonic acid
  参考文献：
  名称：

  Di(1R,2S,5R)-menthyl 2-Hydroxy-3-chloropropylphosphonate 作为一种有用的手性合成子，用于制备对映体纯膦酸

  摘要：

  通过二(1R,2S,5R)-薄荷基酮膦酸酯反应合成立体化学纯的二(1R,2S,5R)-薄荷酯(S)-和(R)-2-羟基-3-氯丙基膦酸酯与由硼氢化钠和（R，R）-（+）-酒石酸或与（S，S）-（-）-酒石酸制备的手性配合物。2-羟基-3-氯丙基膦酸二甲酯被用作制备生物活性产品的chiron。

  DOI：

  10.1055/s-2007-985589

文献信息

• Efficient method for the asymmetric reduction of α- and β-ketophosphonates
  作者：V.V. Nesterov、O.I. Kolodiazhnyi

  DOI：10.1016/j.tet.2007.04.101

  日期：2007.7

  versatile method for the asymmetric reduction of α- and β-ketophosphonates using chiral reactant derived from sodium borohydride and l-(+)- or d-(−)-tartaric acid is developed. The methodology was used for the preparation of a number of biologically interesting enantiomerically pure products: including 2,3-epoxypropylphosphonate 11, 2-hydroxy-3-aminopropylphosphonic acid 14 (phospho-GABOB), phospho-carnitine

  开发了一种高效且通用的方法，该方法使用衍生自硼氢化钠和1-（+）-或d-（-）-酒石酸的手性反应物不对称还原α-和β-酮膦酸酯。该方法被用于许多生物有趣对映体纯产品的制备：含2,3- epoxypropylphosphonate 11，2-羟基-3-氨基丙基膦酸14（磷酸- GABOB），磷酸-肉碱19，和其他在多克规模。
• Di(1<i>R</i>,2<i>S</i>,5<i>R</i>)-menthyl 2-Hydroxy-3-chloropropylphosphonate as a Useful Chiral Synthon for the Preparation of Enantiomerically Pure Phosphonic Acids
  作者：Oleg Kolodiazhnyi、Vitaly Nesterov

  DOI：10.1055/s-2007-985589

  日期：2007.9

  Stereochemically pure di(1 R,2 S,5 R)-menthyl ( S)- and ( R)-2-hydroxy-3-chloropropylphosphonates were synthesized by reaction of di(1 R,2 S,5 R)-menthyl ketophosphonate with chiral complexes prepared from sodium borohydride and ( R, R) -( +)-tartaric acid or with ( S, S)-(-)-tartaric acid. Dimenthyl 2-hydroxy-3-chloropropylphosphonate was utilized as a chiron for the preparation of biologically active

  通过二(1R,2S,5R)-薄荷基酮膦酸酯反应合成立体化学纯的二(1R,2S,5R)-薄荷酯(S)-和(R)-2-羟基-3-氯丙基膦酸酯与由硼氢化钠和（R，R）-（+）-酒石酸或与（S，S）-（-）-酒石酸制备的手性配合物。2-羟基-3-氯丙基膦酸二甲酯被用作制备生物活性产品的chiron。
• Chemoenzymatic Synthesis of Phosphocarnitine Enantiomers
  作者：Marian Mikołajczyk、Jerzy Łuczak、Piotr Kiełbasinski

  DOI：10.1021/jo020330x

  日期：2002.11.1

  starting from diethyl 3-chloro-2-oxopropanephosphonate 4 in three steps involving reduction of 4 to the corresponding 2-hydroxyphosphonate 5, conversion of the latter to phosphonic acid 6, and final reaction with trimethylamine, affording the trimethylammonium salt of 3. Baker's yeast reduction of 4 and enzymatic kinetic resolution of (+/-)-5 afforded the enantiomerically pure precursors of phosphocarnitine

  从3-氯-2-氧代丙烷膦酸二乙酯二乙酯开始，分三步合成外消旋磷酸肉碱3，包括将4还原为相应的2-羟基膦酸酯5，将后者转化为膦酸6，最后与三甲胺反应，得到三甲基铵。 3的盐。贝克酵母还原4和酶动力学拆分（+/-）-5，得到对映体纯的磷酸肉碱，（R）-（+）-5和（S）-（-）-5，分别转化为（S）-（-）-和（R）-（+）-磷酸肉碱3。
• Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride
  作者：V. V. Nesterov、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363206070048

  日期：2006.7

  A method for asymmetric reduction of alpha- and beta-ketophosphonates using a chiral complex prepared from sodium borohydride and D- or L-tartaric acid is developed. Reduction of alpha- or beta-ketophosphonates by these reagents led to formation of corresponding (S)- or (R)-hydroxyphosphonates. Reduction of chiral di(1R,2S,5R)-menthylketophosphonates by the chiral complex NaBH4/(R,R)-tartaric acid due to the dual compliant asymmetric induction resulted in increased stereoselectivity of the reaction and led to formation of the hydroxyphosphonates with ee 90% or higher. On the other hand, reduction of di(1R,2S,5R)-methylketophosphonates by the chiral complex NaBH4/(S,S)-tartaric acid proceeded as non-compliant dual asymmetric induction and resulted in decreased reaction stereoselectivity leading to formation of hydroxyphosphonates with similar to 45-60% ee. The developed methodology was applied to the synthesis of (R)-phosphocarnifine in multigram amounts.
• New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine
  作者：Vitaly V. Nesterov、Oleg I. Kolodiazhnyi

  DOI：10.1016/j.tetasy.2006.03.025

  日期：2006.4

  The reduction of alpha- or beta-ketophosphonates with a chiral reactant 1, prepared from sodium borohydride and (R)- or (S)-tartaric acids, led to the formation of both (S)- and (R)-alpha- or beta-hydroxyphosphonates in high yields. The stereoselectivity of the reaction depended on the absolute configurations of 1 and the ketophosphonates. The reduction of di(1R,2S,5R)-menthyl ketophosphonates with (R)-1 proceeded with matched double asymmetric induction to give high diastereomeric excesses of hydroxyphosphonates (up to 96% de). This methodology was used for the preparation of enantiomerically pure phosphonate modified carnitine on a multigram scale. (c) 2006 Elsevier Ltd. All rights reserved.