1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxymethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 1053299-82-3

• 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: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxymethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1053299-82-3
• 化学式: C₄₈H₆₀N₄O₁₂Si
• 分子量: 913.11
• InChiKey: PBWRAVAHHCRCBA-ZVGMXEIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  65
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxymethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-[(2R,4S,5R)-5-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethoxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and binding properties of pyrimidine oligodeoxynucleoside analogs containing neutral phosphodiester replacements: the formacetal and 3'-thioformacetal internucleoside linkages

  摘要：

  The replacement of the phosphodiester linkage with neutral, achiral, nuclease resistant entities is desirable for the development of oligodeoxynucleotide (ODN) analogs as therapeutic agents in either the antisense or antigene modes. Described herein is the use of the formacetal and 3'-thioformacetal connections as phosphodiester backbone analogs. Pyrimidine dimer blocks containing these moieties were synthesized and incorporated into ODNs in an alternating array with phosphodiester bonds, such that the ODNs had seven acetal and seven phosphodiester linkages. The binding properties of the resulting chimeric ODNs to single-stranded (ss) RNA and double-stranded (ds) DNA were then determined. ssRNA binding properties were determined by thermal denaturation (Tm) analysis, and the 3'-thioformacetal ODN/ssRNA duplex showed a 5.5-degrees-C enhancement in Tm relative to the control phosphodiester ODN. The triple helix formation properties of the 3'-thioformacetal and formacetal ODNs were determined by footprint and restriction enzyme inhibition assays. The 3'-thioformacetal ODN binds to dsDNA with an affinity slightly less than the control ODN. The high affinity and specificity of an ODN containing the 3'-thioformacetal for the ssRNA target and dsDNA target suggest that this linkage is a promising analog for both antisense and triple helix therapeutic applications.

  DOI：

  10.1021/jo00063a014
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine 在 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxymethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  嘧啶（6–4）嘧啶酮光产物类似物的高效化学合成及其性质

  摘要：

  我们合成了具有甲缩醛键的嘧啶（6–4）嘧啶酮光产品的类似物，而不是（6–4）光产品中的磷酸二酯，并研究了针对天然（6–4）光产品的单克隆抗体与含有光产物类似物的DNA。

  DOI：

  10.1016/s0040-4039(00)00127-1

文献信息

• Efficient chemical synthesis of a pyrimidine (6–4) pyrimidone photoproduct analog and its properties
  作者：Kousuke Satou、Yasuo Komatsu、Takuya Torizawa、Koichi Kato、Ichio Shimada、Osamu Nikaido、Eiko Ohtsuka

  DOI：10.1016/s0040-4039(00)00127-1

  日期：2000.3

  We synthesized an analog of a pyrimidine (6–4) pyrimidone photoproduct with a formacetal linkage instead of the phosphodiester in the (6–4) photoproduct, and investigated the interaction between a monoclonal antibody specific to the natural (6–4) photoproduct and a DNA containing the photoproduct analog.

  我们合成了具有甲缩醛键的嘧啶（6–4）嘧啶酮光产品的类似物，而不是（6–4）光产品中的磷酸二酯，并研究了针对天然（6–4）光产品的单克隆抗体与含有光产物类似物的DNA。
• Synthesis and binding properties of pyrimidine oligodeoxynucleoside analogs containing neutral phosphodiester replacements: the formacetal and 3'-thioformacetal internucleoside linkages
  作者：Robert J. Jones、Kuei Ying Lin、John F. Milligan、Shalini Wadwani、Mark D. Matteucci

  DOI：10.1021/jo00063a014

  日期：1993.5

  The replacement of the phosphodiester linkage with neutral, achiral, nuclease resistant entities is desirable for the development of oligodeoxynucleotide (ODN) analogs as therapeutic agents in either the antisense or antigene modes. Described herein is the use of the formacetal and 3'-thioformacetal connections as phosphodiester backbone analogs. Pyrimidine dimer blocks containing these moieties were synthesized and incorporated into ODNs in an alternating array with phosphodiester bonds, such that the ODNs had seven acetal and seven phosphodiester linkages. The binding properties of the resulting chimeric ODNs to single-stranded (ss) RNA and double-stranded (ds) DNA were then determined. ssRNA binding properties were determined by thermal denaturation (Tm) analysis, and the 3'-thioformacetal ODN/ssRNA duplex showed a 5.5-degrees-C enhancement in Tm relative to the control phosphodiester ODN. The triple helix formation properties of the 3'-thioformacetal and formacetal ODNs were determined by footprint and restriction enzyme inhibition assays. The 3'-thioformacetal ODN binds to dsDNA with an affinity slightly less than the control ODN. The high affinity and specificity of an ODN containing the 3'-thioformacetal for the ssRNA target and dsDNA target suggest that this linkage is a promising analog for both antisense and triple helix therapeutic applications.