[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl] trifluoromethanesulfonate | 152685-35-3

• 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: [[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl] trifluoromethanesulfonate
• CAS: 152685-35-3
• 化学式: C₃₈H₄₅F₃N₂O₁₀SSi
• 分子量: 806.929
• InChiKey: LRHDVEKZVQVQRW-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl] trifluoromethanesulfonate 在 咪唑 、 2,6-二叔丁基-4-甲基吡啶 作用下， 反应 3.0h， 生成 1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Diisopropylsilyl-linked oligonucleotide analogs: solid-phase synthesis and physicochemical properties

  摘要：

  A novel synthetic method has been developed for efficient preparation of silyl-linked oligodeoxyribonucleotide analogs. The method allows, for the first time, automated solid-phase synthesis of long oligomers uniformly linked with the silyl internucleoside bridge. Synthesis of a thymidylate decanucleotide analog (14) illustrates this advance. The preparation of chimeric oligodeoxyribonucleotides containing single or multiple diisopropylsilyl backbone structures along with natural phosphodiester links is also described. These mixed backbone DNA strands were soluble and chemically stable in buffered aqueous solutions, as required for physicochemical study. These oligomers demonstrated excellent stability toward cleavage by 3'-exonuclease and good binding affinity with complementary oligonucleotides.

  DOI：

  10.1021/jo00079a030
• 作为产物：
  描述：

  diisopropylsilanediyl bistriflate 、 保护胸苷 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 [[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-di(propan-2-yl)silyl] trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of dendritic oligodeoxyribonucleotide analogs with nonionic diisopropylsilyl linkage

  摘要：

  Series of new dendritic oligodeoxyribonucleotide analogs with diisopropylsilyl linkage were prepared via liquid-phase synthesis. Dendron was employed as soluble support, which facilitated purification of the products by simple solvent precipitation. Sequences leading to the dendritic octamer 5'-TSiTSiTSiTSiTSiT-(Si)T(Si)T(S)2-3' (T8D(2)) were prepared and each isolated intermediate was characterized by NMR and mass spectrometry. The recognition properties of two complementary dendritic dinucleotide analogs of TSiTSiD2 (T2D2) and A(Si)A(Si)D(2) (A2D(2)) were also studied by NMR and FT-MS spectra in a nonaqueous aprotic environment (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.108

文献信息

• Synthesis of dendritic oligodeoxyribonucleotide analogs with nonionic diisopropylsilyl linkage
  作者：Jin-Liang Lv、Zhi-Yong Zhao、Zhong-Qiang Yang、Dong-Sheng Liu、Qing-Hua Fan

  DOI：10.1016/j.tet.2011.09.108

  日期：2011.11

  Series of new dendritic oligodeoxyribonucleotide analogs with diisopropylsilyl linkage were prepared via liquid-phase synthesis. Dendron was employed as soluble support, which facilitated purification of the products by simple solvent precipitation. Sequences leading to the dendritic octamer 5'-TSiTSiTSiTSiTSiT-(Si)T(Si)T(S)2-3' (T8D(2)) were prepared and each isolated intermediate was characterized by NMR and mass spectrometry. The recognition properties of two complementary dendritic dinucleotide analogs of TSiTSiD2 (T2D2) and A(Si)A(Si)D(2) (A2D(2)) were also studied by NMR and FT-MS spectra in a nonaqueous aprotic environment (C) 2011 Elsevier Ltd. All rights reserved.
• Diisopropylsilyl-linked oligonucleotide analogs: solid-phase synthesis and physicochemical properties
  作者：Ashis K. Saha、Mark Sardaro、Cheryl Waychunas、Daniel Delecki、L. I. Kruse、Rusty Kutny、Paul Cavanaugh、Anne Yawman、Donald A. Upson

  DOI：10.1021/jo00079a030

  日期：1993.12

  A novel synthetic method has been developed for efficient preparation of silyl-linked oligodeoxyribonucleotide analogs. The method allows, for the first time, automated solid-phase synthesis of long oligomers uniformly linked with the silyl internucleoside bridge. Synthesis of a thymidylate decanucleotide analog (14) illustrates this advance. The preparation of chimeric oligodeoxyribonucleotides containing single or multiple diisopropylsilyl backbone structures along with natural phosphodiester links is also described. These mixed backbone DNA strands were soluble and chemically stable in buffered aqueous solutions, as required for physicochemical study. These oligomers demonstrated excellent stability toward cleavage by 3'-exonuclease and good binding affinity with complementary oligonucleotides.