diethyl (R)-(-)-2,3-dihydroxypropylphosphonate | 23737-49-7

• 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 (R)-(-)-2,3-dihydroxypropylphosphonate
• 英文别名: diethyl [(R)-3,4-dihydroxypropyl]phosphonate；diethyl (R)-2,3-dihydroxypropylphosphonate；diethyl 2(R),3-dihydroxypropylphosphonate；(2R)-3-diethoxyphosphorylpropane-1,2-diol
• CAS: 23737-49-7
• 化学式: C₇H₁₇O₅P
• 分子量: 212.183
• InChiKey: LNBBUKIQJDFSRJ-SSDOTTSWSA-N

物化性质

• 沸点：
  364.1±32.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (R)-(-)-2,3-dihydroxypropylphosphonate 在 盐酸 、 牛血清白蛋白 作用下， 以 吡啶 为溶剂， 反应 70.5h， 生成 diethyl 3-(N,O-diethyloxycarbonylhydroxyamino)-2(R)-hydroxypropylphosphonate
  参考文献：
  名称：

  Studies on phosphonic acid antibiotics. III. Structure and synthesis of 3-(N-acetyl-N-hydroxyamino)propylphosphonic acid (FR-900098) and 3-(N-acetyl-N-hydroxyamino)-2(R)-hydroxypropylphosphonic acid (FR-33289)

  摘要：

  从红斑链霉菌中分离出来的抗生素 FR-900098 (II) 和 FR-33289 (III) 的结构已确定为 3-(N-乙酰基-N-羟氨基)-丙基膦酸和 3-(N-乙酰基- N-羟基氨基)-2(R)-羟丙基膦酸，分别基于光谱和化学证据，最后通过合成。

  DOI：

  10.1248/cpb.29.646
• 作为产物：
  描述：

  2,3-环氧丙基膦酸二乙基酯 在 (S,S)-(salen)cobalt(III)(OAc) 、 水 作用下， 生成 diethyl (R)-(-)-2,3-dihydroxypropylphosphonate
  参考文献：
  名称：

  Towards enantiomeric 2,3-epoxypropylphosphonates †Dedicated to Professor Jan Michalski on the occasion of his 80th birthday. †

  摘要：

  Hydrolysis of diethyl 2,3-epoxypropylphosphonate in the presence of (R,R)-salen-Co(III)-OAc after 19 h afforded a mixture of (S)-epoxide (82% ee) and diethyl (R)-2,3-dihydroxypropylphosphonate (98% ee). Improved enantiomeric excess (93%) of the (S)-epoxide was obtained in the 72 h hydrolytic kinetic resolution experiment. Acid-catalyzed hydrolysis of (S)-epoxide (91% ee) gave (S)-diol (72% ee) due to low C-3 regioselectivity of the reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00171-3

文献信息

• Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors
  作者：Mahipal Yadav、Riya Raghupathy、Varma Saikam、Saidulu Dara、Parvinder Pal Singh、Sanghapal D. Sawant、Satyajit Mayor、Ram A. Vishwakarma

  DOI：10.1039/c3ob42116c

  日期：——

  Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-3,4-bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1-phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with

  第一代不可水解的C-GPI膦酸酯类似物，合成v IZ，6-。ø - （2-氨基-2-脱氧-3-α- d吡喃葡萄糖基） - d -肌醇肌醇-1- Ö - （SN - 3,4-双（棕榈酰氧基）丁基-1-膦酸盐）23A和6- ø - （2-氨基-2-脱氧-3-α- d吡喃葡萄糖基） - d -肌醇肌醇-1- ö - （SN -2据报道，（3-双（棕榈酰氧基）丙基-1-膦酸酯）23b。通过将α-假二糖21与膦酸偶联来合成目标化合物分别以定量收率得到18a和18b，然后脱保护。这些合成的C-膦酸酯GPI探针对磷脂酰肌醇特异性磷脂酶C（PI-PLC）具有抗性，并且还显示出对酶活性的中等抑制作用。
• 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)
• An efficient synthesis of enantiomerically pure diethyl 2,3-dihydroxypropylphosphonate
  作者：Andrzej E. Wróblewski、Anetta Hałajewska-Wosik

  DOI：10.1016/j.tetasy.2004.05.039

  日期：2004.7

  A reliable method for the synthesis of the enantiomerically Pure diethyl (R)-2,3-dihydroxypropylphosphonate from 1,2:5.6-di-O-cyclohexylidene-D-mannitol is elaborated. (C) 2004 Elsevier Ltd. All rights reserved.
• Phosphonate Lipid Tubules II
  作者：Britt N. Thomas、Christopher M. Lindemann、Robert C. Corcoran、Casey L. Cotant、Janet E. Kirsch、Phillip J. Persichini

  DOI：10.1021/ja012137a

  日期：2002.2.1

  We describe a new chiral tubule-forming lipid in which the C-O-P phosphoryl linkage of the archetypal tubule-forming molecule, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, "DC(8,9)PC", is replaced by a C-P linkage. Tubule formation with this phosphonate analogue proceeds under the same mild conditions as with DC(8,9)PC and produces similar yields, but synchrotron small-angle X-ray scattering, atomic force microscopy, and optical microscopy show the new tubules to have diameters 1.94 times as great, to be significantly shorter, and to be thinner-walled. A significant portion of the enantiomerically pure chiral phosphonate precipitate is in the form of stable open helices, and these helices are divided almost evenly between left- and right-handed members.
• Studies on phosphonic acid antibiotics. II. Synthesis of 3-(n-acetyl-n-hydroxyamino)-2(r)-hydroxypropylphosphonic acid (FR-33289) and 3-(n-formyl-n-hydroxyamino)-1--propenylphosphonic acid (FR-32863)
  作者：Masashi Hashimoto、Keiji Hemmi、Hidekazu Takeno、Takashi Kamiya

  DOI：10.1016/s0040-4039(00)93634-7

  日期：1980.1