[(3S)-3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)-oxidophosphaniumyl]oxy-3-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]propyl] 4-methylbenzenesulfonate | 494798-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(3S)-3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)-oxidophosphaniumyl]oxy-3-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]propyl] 4-methylbenzenesulfonate
• CAS: 494798-48-0
• 化学式: C₆₉H₇₆N₅O₁₇PSSi
• 分子量: 1338.51
• InChiKey: BITCTNNFLBEEEI-NIBRQSQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  94
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  281
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  [(3S)-3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)-oxidophosphaniumyl]oxy-3-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]propyl] 4-methylbenzenesulfonate 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Diastereoselective Synthesis of a Conformationally Restricted Dinucleotide with Predefined α and β Torsional Angles for the Construction of α,β-Constrained Nucleic Acids (α,β-CNA)

  摘要：

  [GRAPHICS]The synthesis of a diastereopure 1,3,2-dioxaphosphorinane linkage in which two, alpha and beta, out of six torsion angles of the natural phosphodiester backbone are constrained with predefined values of ca. +60degrees (g+) and 180degrees (t), respectively, is described. The stable and unstrained six-membered cyclic phosphotriester structure represents the smallest possible ring allowing the conformational locking of the alpha torsion angle at a significant positive value that is typical of many bulged regions of nucleic acids.

  DOI：

  10.1021/ol027222h
• 作为产物：
  描述：

  1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 在 吡啶 、 四氮唑 、 bismuth(III) chloride 、 sodium tetrahydroborate 、 zinc(II) iodide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 26.33h， 生成 [(3S)-3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)-oxidophosphaniumyl]oxy-3-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]propyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  Diastereoselective Synthesis of a Conformationally Restricted Dinucleotide with Predefined α and β Torsional Angles for the Construction of α,β-Constrained Nucleic Acids (α,β-CNA)

  摘要：

  [GRAPHICS]The synthesis of a diastereopure 1,3,2-dioxaphosphorinane linkage in which two, alpha and beta, out of six torsion angles of the natural phosphodiester backbone are constrained with predefined values of ca. +60degrees (g+) and 180degrees (t), respectively, is described. The stable and unstrained six-membered cyclic phosphotriester structure represents the smallest possible ring allowing the conformational locking of the alpha torsion angle at a significant positive value that is typical of many bulged regions of nucleic acids.

  DOI：

  10.1021/ol027222h

文献信息

• Diastereoselective Synthesis of a Conformationally Restricted Dinucleotide with Predefined α and β Torsional Angles for the Construction of α,β-Constrained Nucleic Acids (α,β-CNA)
  作者：Ingrid Le Clézio、Jean-Marc Escudier、Alain Vigroux

  DOI：10.1021/ol027222h

  日期：2003.1.1

  [GRAPHICS]The synthesis of a diastereopure 1,3,2-dioxaphosphorinane linkage in which two, alpha and beta, out of six torsion angles of the natural phosphodiester backbone are constrained with predefined values of ca. +60degrees (g+) and 180degrees (t), respectively, is described. The stable and unstrained six-membered cyclic phosphotriester structure represents the smallest possible ring allowing the conformational locking of the alpha torsion angle at a significant positive value that is typical of many bulged regions of nucleic acids.