(S)-diethyl[O-3,4-isopropylidene-3,4-dihydroxybutyl]phosphonate | 56119-82-5

• 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[O-3,4-isopropylidene-3,4-dihydroxybutyl]phosphonate
• 英文别名: (4S)-4-(2-diethoxyphosphorylethyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 56119-82-5
• 化学式: C₁₁H₂₃O₅P
• 分子量: 266.274
• InChiKey: UDCQBOUEGTURMW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-diethyl[O-3,4-isopropylidene-3,4-dihydroxybutyl]phosphonate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (S)-diethyl(3,4-dihydroxybutyl)phosphonate
  参考文献：
  名称：

  糖基磷脂酰肌醇（GPI）锚的不可水解模拟物的合成†

  摘要：

  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。

  DOI：

  10.1039/c3ob42116c
• 作为产物：
  描述：

  (S)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (S)-diethyl[O-3,4-isopropylidene-3,4-dihydroxybutyl]phosphonate
  参考文献：
  名称：

  糖基磷脂酰肌醇（GPI）锚的不可水解模拟物的合成†

  摘要：

  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。

  DOI：

  10.1039/c3ob42116c

文献信息

• Design, Synthesis, and Evaluation of Phospholipid Analogs as Inhibitors of the Bacterial Phospholipase C from Bacillus cereus
  作者：Stephen F. Martin、Yue-Ling Wong、Allan S. Wagman

  DOI：10.1021/jo00096a024

  日期：1994.8

  Enzymes belonging to the phospholipase C (PLC) family hydrolyze the phosphodiester bond of phospholipids to give a diacylglycerol and a phosphorylated head group. The bacterial phospholipase C from Bacillus cereus (PLC(Bc)) has been studied extensively, and there is a wealth of information regarding those structural features that are important for substrate activity. In contrast, there is virtually no data available regarding structure-activity relationships for inhibitors of this enzyme. To address this shortcoming, a series of optically pure analogues of 1,2-dihexanoyl-sn-glycero-3-phosphocholine (2) containing different replacements of the phosphate group were first synthesized including the phosphoramidates 4 and 8, the phosphonate 5, the (difluoromethylene)phosphonate 6, the thiophosphate 7, the diastereomeric phosphorothioates 9 and 10, and the phosphorodithioate 11. Each of these phosphatidylcholine derivatives was tested for inhibitor or substrate activity with PLC(Bc) using the water-soluble phosphatidylcholine 2 as the monomeric substrate. The measurements were conducted below the critical micellar concentrations of both 2 and the inhibitor. Of the analogues, only 7 and 9 underwent observable enzymatic hydrolysis under the assay conditions used. The k(cat) of the (Sp)-phosphorothioate 9 was approximately one-fifth that of 2, and when compared to 2, 7 was hydrolyzed only very slowly by the enzyme. Kinetic studies indicated that the phospholipid analogues tested were competitive inhibitors with increasing K-i's follows: 7 approximate to 11 approximate to 10 < 4 approximate to 8 < 5 approximate to 6.
• Phosphonate Lipid Tubules. 1
  作者：B. N. Thomas、R. C. Corcoran、C. L. Cotant、C. M. Lindemann、J. E. Kirsch、P. J. Persichini

  DOI：10.1021/ja973933c

  日期：1998.12.1

  We describe a new chiral tubule-forming lipid in which the C-O-P headgroup/glycerol backbone Linkage of the archetypal tubule-forming phospholipid, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, DC(8,9)PC, is replaced by a C-C-P linkage. Tubule formation from this phosphonate analogue occurs under the same mild conditions as with DC(8,9)PC and produces identical yields, but the phosphonate tubules have cylindrical diameters twice that of DC(8,9)PC tubules. Small-angle X-ray scattering, atomic-force, and optical microscopy reveal the new tubules to consist of fewer coaxially nested cylindrical lamellae than DC(8,9)PC tubules; accordingly, the phosphonate tubules are more fragile. In addition, a small portion of the phosphonate precipitate is in the form of stable open helices, and enantiomerically pure preparations of the new molecule contain significant numbers of helices possessing the unexpected sense of handedness.
• Paulsen,H.; Bartsch,W., Chemische Berichte, 1975, vol. 108, p. 1745 - 1755
  作者：Paulsen,H.、Bartsch,W.

  DOI：——

  日期：——
• 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。