2',5'-Di(tert-butyldimethylsilyl)-3'-(ethyl 4-formylphenyl phosphate)uridine | 1053738-03-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: 2',5'-Di(tert-butyldimethylsilyl)-3'-(ethyl 4-formylphenyl phosphate)uridine
• 英文别名: [(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] ethyl (4-formylphenyl) phosphate
• CAS: 1053738-03-6
• 化学式: C₃₀H₄₉N₂O₁₀PSi₂
• 分子量: 684.871
• InChiKey: SEEXNYNSSILLRL-BQSQRIDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',5'-Di(tert-butyldimethylsilyl)-3'-(ethyl 4-formylphenyl phosphate)uridine 在 sodium tetrahydroborate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 2',5'-Di(tert-butyldimethylsilyl)-3'-(ethyl 4-(fluoromethyl)phenyl phosphate)uridine
  参考文献：
  名称：

  Mechanism-based inactivation of ribonuclease A

  摘要：

  The first example of a mechanism-based inhibitor of a phosphodiesterase is reported. Although the inactivation brought about by the fluoride 4 is not complete, this compound provides a useful starting point for the synthesis of other more potent inhibitors of ribonuclease A, as well as inhibitors of other nucleases. In addition, an inexpensive method is described for the synthesis of phosphate diesters that cannot be synthesized using standard phosphoramidite methodology. Phosphitylation of the target alcohol with a dialkyl chlorophosphite, followed by activation of the resulting trialkyl phosphite with It, yields an iodophosphate. The resulting iodophosphate can then be coupled to a second alcohol, phenol, or enolate to give a phosphate triester, which after subsequent deprotection affords the desired phosphate diester. The novel phosphorylation chemistry presented should greatly facilitate the synthesis of other similar mechanism-based phosphodiesterase inhibitors.

  DOI：

  10.1021/jo00126a051
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] diethyl phosphite 在 吡啶 、 盐酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 2',5'-Di(tert-butyldimethylsilyl)-3'-(ethyl 4-formylphenyl phosphate)uridine
  参考文献：
  名称：

  Mechanism-based inactivation of ribonuclease A

  摘要：

  The first example of a mechanism-based inhibitor of a phosphodiesterase is reported. Although the inactivation brought about by the fluoride 4 is not complete, this compound provides a useful starting point for the synthesis of other more potent inhibitors of ribonuclease A, as well as inhibitors of other nucleases. In addition, an inexpensive method is described for the synthesis of phosphate diesters that cannot be synthesized using standard phosphoramidite methodology. Phosphitylation of the target alcohol with a dialkyl chlorophosphite, followed by activation of the resulting trialkyl phosphite with It, yields an iodophosphate. The resulting iodophosphate can then be coupled to a second alcohol, phenol, or enolate to give a phosphate triester, which after subsequent deprotection affords the desired phosphate diester. The novel phosphorylation chemistry presented should greatly facilitate the synthesis of other similar mechanism-based phosphodiesterase inhibitors.

  DOI：

  10.1021/jo00126a051

文献信息

• Mechanism-based inactivation of ribonuclease A
  作者：Jeffrey K. Stowell、Theodore S. Widlanski、Tatiana G. Kutateladze、Ronald T. Raines

  DOI：10.1021/jo00126a051

  日期：1995.10

  The first example of a mechanism-based inhibitor of a phosphodiesterase is reported. Although the inactivation brought about by the fluoride 4 is not complete, this compound provides a useful starting point for the synthesis of other more potent inhibitors of ribonuclease A, as well as inhibitors of other nucleases. In addition, an inexpensive method is described for the synthesis of phosphate diesters that cannot be synthesized using standard phosphoramidite methodology. Phosphitylation of the target alcohol with a dialkyl chlorophosphite, followed by activation of the resulting trialkyl phosphite with It, yields an iodophosphate. The resulting iodophosphate can then be coupled to a second alcohol, phenol, or enolate to give a phosphate triester, which after subsequent deprotection affords the desired phosphate diester. The novel phosphorylation chemistry presented should greatly facilitate the synthesis of other similar mechanism-based phosphodiesterase inhibitors.