(S)-2-hydroxy-3-(N,N,N-trimethylammonium)phosphonic acid | 476493-48-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-hydroxy-3-(N,N,N-trimethylammonium)phosphonic acid
• 英文别名: (S)-(-)-phosphocarnitine；(S)-phosphocarnitine；phosphocarnitine；hydrogen [(2S)-2-hydroxy-3-(trimethylazaniumyl)propyl]phosphonate；hydroxy-[(2S)-2-hydroxy-3-(trimethylazaniumyl)propyl]phosphinate
• CAS: 476493-48-8
• 化学式: C₆H₁₆NO₄P
• mdl: MFCD09863811
• 分子量: 197.171
• InChiKey: CFKIUJQHVVMWGR-LURJTMIESA-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-(diethoxyphosphoryl)-2-hydroxy-N,N,N-trimethylpropyl-ammonium bromide 在 4-二甲氨基吡啶 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 77.0h， 生成 (S)-2-hydroxy-3-(N,N,N-trimethylammonium)phosphonic acid
  参考文献：
  名称：

  对映体 (S)-磷酸肉碱的有效合成

  摘要：

  (S)-2,3-环氧丙基膦酸二乙酯 [(S)-3] 在以下反应序列中转化为 (S)-磷酸肉碱 [(S)-2]：环氧乙烷环的 C-3 区域选择性打开与溴化镁、用三甲胺定量溴化物置换和酯水解。3用HCl/EtOAc的环氧化物开环得到3-和2-氯-取代的膦酸酯的92:8混合物。(S)-3与NMe3水溶液的反应得到3-羟基-1-丙烯基膦酸二乙酯作为主要产物。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200208)2002:16<2758::aid-ejoc2758>3.0.co;2-q

文献信息

• 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 Methods and Strategies for Asymmetric Synthesis of Organophosphorus Compounds
  作者：O. I. Kolodiazhnyi、I. V. Guliayko、E. V. Gryshkun、A. O. Kolodiazhna、V. V. Nesterov、G. O. Kachkovskyi

  DOI：10.1080/10426500701735320

  日期：2008.1.14

  New methods for the asymmetric synthesis of organophosphorus compounds were developed and applied for the preparation of a number of biologically important enantiomerically pure products.
• An Efficient Synthesis of Enantiomeric (S)-Phosphocarnitine
  作者：Andrzej E. Wróblewski、Anetta Hałajewska-Wosik

  DOI：10.1002/1099-0690(200208)2002:16<2758::aid-ejoc2758>3.0.co;2-q

  日期：2002.8

  Diethyl (S)-2,3-epoxypropylphosphonate [(S)-3] was transformed into (S)-phosphocarnitine [(S)-2] in the following sequence of reactions: a C-3 regioselective opening of the oxirane ring with magnesium bromide, quantitative bromide displacement with trimethylamine, and ester hydrolysis. The epoxide ring opening of 3 with HCl/EtOAc gave a 92:8 mixture of 3- and 2-chloro-substituted phosphonates. Reaction

  (S)-2,3-环氧丙基膦酸二乙酯 [(S)-3] 在以下反应序列中转化为 (S)-磷酸肉碱 [(S)-2]：环氧乙烷环的 C-3 区域选择性打开与溴化镁、用三甲胺定量溴化物置换和酯水解。3用HCl/EtOAc的环氧化物开环得到3-和2-氯-取代的膦酸酯的92:8混合物。(S)-3与NMe3水溶液的反应得到3-羟基-1-丙烯基膦酸二乙酯作为主要产物。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)