Diethyl (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxypentanephosphonate | 150934-80-8

• 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 (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxypentanephosphonate
• 英文别名: diethyl (3S,4S)-4,5-O-isopropylidene-3,4,5-trihydroxypentanephosphonate；(1S)-3-[diethoxy(oxido)phosphaniumyl]-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol
• CAS: 150934-80-8
• 化学式: C₁₂H₂₅O₆P
• 分子量: 296.301
• InChiKey: ZWUHRTHUZJAYKT-QWRGUYRKSA-N

物化性质

• 沸点：
  398.2±27.0 °C(predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基膦酸二乙酯 、 (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以65%的产率得到Diethyl (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxypentanephosphonate
  参考文献：
  名称：

  A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides

  摘要：

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.

  DOI：

  10.1021/jo00073a043

文献信息

• A facile synthesis of β- and γ- hydroxyphosphonate esters from epoxides
  作者：Saibaba Racha、Zhengong Li、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1016/s0040-4039(00)61125-5

  日期：1992.9

  A BF3.OEt2 catalyzed, regiospecific nucleophilic ring opening reaction of epoxides by dialkyl phosphite and methanephosphonate esters is described. The reaction proceeds in good to excellent yields to give the title compounds and is compatible with a variety of other functional groups.

  描述了BF 3 .OEt 2催化的亚磷酸二烷基酯和甲膦酸酯的环氧化物的区域特异性亲核开环反应。反应以良好的收率进行，得到优异的标题化合物，并且与多种其他官能团相容。
• A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides
  作者：Zhengong Li、Saibaba Racha、Li Dan、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1021/jo00073a043

  日期：1993.10

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.