2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid | 164254-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid
• CAS: 164254-08-4
• 化学式: C₂₇H₃₂N₂O₆Si
• 分子量: 508.646
• InChiKey: RWLRYQHIOXTGMB-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid 在 二异丙基铵盐四氮唑 、 四丁基氟化铵 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.5h， 生成
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by an amide: Effect of backbone length on duplex stability with RNA complement

  摘要：

  Five dimers containing amide linkages instead of the natural phosphodiester linkage were synthesized and incorporated into oligonucleotides. The length of the amide backbone was varied. The hybridization properties of the modified oligonucleotides with RNA complements and their conformational analysis are described and compared to previously reported amide containing oligonucleotides. In addition, the synthesis of a thioamide phosphoramidite dimer is reported. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00037-1
• 作为产物：
  描述：

  1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil 在 sodium hydroxide 、 mercury dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]acetic acid
  参考文献：
  名称：

  Comparison of two amides as backbone replacement of the phosphodiester linkage in oligodeoxynucleotides

  摘要：

  The two isomeric amide modifications 1 and 2 show similar effects on the melting temperature of RNA/DNA duplexes, when they replace the natural phosphodiester linkage in the DNA strand. The synthesis of the amide dimer 1 is presented.

  DOI：

  10.1016/s0040-4039(00)77069-9

文献信息

• Comparison of two amides as backbone replacement of the phosphodiester linkage in oligodeoxynucleotides
  作者：Jacques Lebreton、Adrian Waldner、Valérie Fritsch、Romain M. Wolf、Alain De Mesmaeker

  DOI：10.1016/s0040-4039(00)77069-9

  日期：1994.7

  The two isomeric amide modifications 1 and 2 show similar effects on the melting temperature of RNA/DNA duplexes, when they replace the natural phosphodiester linkage in the DNA strand. The synthesis of the amide dimer 1 is presented.
• Replacement of the phosphodiester linkage in oligonucleotides by an amide: Effect of backbone length on duplex stability with RNA complement
  作者：Alain De Mesmaeker、Chantal Jouanno、Romain M. Wolf、Sebastian Wendeborn

  DOI：10.1016/s0960-894x(97)00037-1

  日期：1997.2

  Five dimers containing amide linkages instead of the natural phosphodiester linkage were synthesized and incorporated into oligonucleotides. The length of the amide backbone was varied. The hybridization properties of the modified oligonucleotides with RNA complements and their conformational analysis are described and compared to previously reported amide containing oligonucleotides. In addition, the synthesis of a thioamide phosphoramidite dimer is reported. (C) 1997, Elsevier Science Ltd.