2-cyanoethyl [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl diisopropylamidophosphite | 205533-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyanoethyl [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl diisopropylamidophosphite
• 英文别名: 3-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 205533-35-3
• 化学式: C₁₅H₂₉N₂O₄P
• 分子量: 332.38
• InChiKey: DFPMNXKYVHLIAD-HNNQXCQYSA-N

物化性质

• 沸点：
  355.9±27.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl diisopropylamidophosphite 、 N²-isobutyryl acyclovir 在 四氮唑 、 ammonium hydroxide 、 碘 、 溶剂黄146 作用下， 生成 Phosphoric acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester (R)-2,3-dihydroxy-propyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Lysophosphatidylnucleosides

  摘要：

  5'-O-Lysophosphatidylnucleosides [5'-O-(1-O-acyl-sn-glycero-3-phosphoryl)nucleosides] were obtained by a two-step chemoenzymatic synthesis. 5'-O-(sn-Glycero-3-phosphoryl)nucleosides (5'-GPNs) were first prepared from a phosphoramidite of 1,2-O-isopropylidene-sn-glycerol and appropriately protected nucleosides, applying the phosphoramidite methodology on the solid phase or in solution. In a following step, the regioselective acylation at the C-l hydroxyl of the glycerol moiety of 5'-GPNs was achieved by a lipase-catalyzed transacylation with activated fatty acid esters in organic solvent. Some deoxyribo- and ribonucleosides, as well, were converted into the corresponding lysophosphatidyl derivatives utilizing either saturated or unsaturated fatty acid esters with different length alkyl chains. The synthesis was also applied to the preparation of O-(1-O-palmitoyl-sn-glycero-3-phosphoryl) conjugates of Acyclovir and AZT, of potential pharmacological interest.

  DOI：

  10.1021/jo971826v
• 作为产物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 (S)-(+)-1,2-异亚丙基甘油 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以90%的产率得到2-cyanoethyl [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl diisopropylamidophosphite
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Lysophosphatidylnucleosides

  摘要：

  5'-O-Lysophosphatidylnucleosides [5'-O-(1-O-acyl-sn-glycero-3-phosphoryl)nucleosides] were obtained by a two-step chemoenzymatic synthesis. 5'-O-(sn-Glycero-3-phosphoryl)nucleosides (5'-GPNs) were first prepared from a phosphoramidite of 1,2-O-isopropylidene-sn-glycerol and appropriately protected nucleosides, applying the phosphoramidite methodology on the solid phase or in solution. In a following step, the regioselective acylation at the C-l hydroxyl of the glycerol moiety of 5'-GPNs was achieved by a lipase-catalyzed transacylation with activated fatty acid esters in organic solvent. Some deoxyribo- and ribonucleosides, as well, were converted into the corresponding lysophosphatidyl derivatives utilizing either saturated or unsaturated fatty acid esters with different length alkyl chains. The synthesis was also applied to the preparation of O-(1-O-palmitoyl-sn-glycero-3-phosphoryl) conjugates of Acyclovir and AZT, of potential pharmacological interest.

  DOI：

  10.1021/jo971826v

文献信息

• Synthesis of 3′(2′)-O-Lysophosphatidylnucleosides − a Further Application of a Chemoenzymatic Strategy
  作者：Rosa Chillemi、Danilo Aleo、Giuseppe Granata、Sebastiano Sciuto

  DOI：10.1002/1099-0690(200211)2002:21<3622::aid-ejoc3622>3.0.co;2-4

  日期：2002.11

  for the preparation of 3′-O-lysophosphatidyl derivatives of 5′-deoxy-5-fluorouridine and 5′-deoxy-5′-(methylthio)adenosine, with the 2′-O-isomer of the latter compound also being prepared. The enhanced ability of lysophosphatidyl compounds to interact with lipid monolayers was also tested in comparison with that of the relevant free nucleosides. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DNA 的四个 3'-核苷酸的单[(2R)-2,3-二氢丙基]酯，由受保护的核苷亚磷酰胺和 [(4S)-2,2-二甲基-1,3-二氧戊环-4-基] 制备甲醇，在甘油部分的 C-1 羟基处通过脂肪酶催化的转酰基作用与有机溶剂中的活化棕榈酸酯进行区域选择性酰化，得到相关的 3'-O-溶血磷脂酰-2'-脱氧核苷。该合成还适用于制备 5'-脱氧-5-氟尿苷和 5'-脱氧-5'-（甲硫基）腺苷的 3'-O-溶血磷脂酰衍生物，后者的 2'-O-异构体化合物也在制备中。与相关游离核苷的能力相比，还测试了溶血磷脂酰化合物与脂质单层相互作用的增强能力。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Chemoenzymatic Synthesis of Lysophosphatidylnucleosides
  作者：Rosa Chillemi、Domenico Russo、Sebastiano Sciuto

  DOI：10.1021/jo971826v

  日期：1998.5.1

  5'-O-Lysophosphatidylnucleosides [5'-O-(1-O-acyl-sn-glycero-3-phosphoryl)nucleosides] were obtained by a two-step chemoenzymatic synthesis. 5'-O-(sn-Glycero-3-phosphoryl)nucleosides (5'-GPNs) were first prepared from a phosphoramidite of 1,2-O-isopropylidene-sn-glycerol and appropriately protected nucleosides, applying the phosphoramidite methodology on the solid phase or in solution. In a following step, the regioselective acylation at the C-l hydroxyl of the glycerol moiety of 5'-GPNs was achieved by a lipase-catalyzed transacylation with activated fatty acid esters in organic solvent. Some deoxyribo- and ribonucleosides, as well, were converted into the corresponding lysophosphatidyl derivatives utilizing either saturated or unsaturated fatty acid esters with different length alkyl chains. The synthesis was also applied to the preparation of O-(1-O-palmitoyl-sn-glycero-3-phosphoryl) conjugates of Acyclovir and AZT, of potential pharmacological interest.