[4-(5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate | 689260-64-8

• 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: [4-(5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate
• 英文别名: [4-[(2S,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,4-dihydroxyoxolan-2-yl]imidazol-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 689260-64-8
• 化学式: C₃₅H₄₀N₂O₈
• 分子量: 616.711
• InChiKey: HCXVZDNRVDVUKN-ANLCFORVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 [4-(5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate 以 吡啶 为溶剂， 生成 [4-[(2S,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]imidazol-1-yl]methyl 2,2-dimethylpropanoate 、 [4-[(2S,3S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoxolan-2-yl]imidazol-1-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite: A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes

  摘要：

  A high-yielding synthetic route leading to new 2'-O-cyanoethylated imidazole C-ribonucleoside phosphoramidite (PA) 1 has been developed (41% overall yield in ten steps). This has resulted in a marked improvement of yield compared to unstable 2'-O-TBDMS PA 2. The new synthon PA 1 enables the imidazole moiety to be incorporated into any RNA sequence in principle, and has been used as a practical building block for probing the catalytic mechanism of a ribozyme.

  DOI：

  10.3987/com-10-11978
• 作为产物：
  描述：

  4(5)-2,3,5-tri-O-benzyl-β-D-ribofuranosylimidazole 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 [4-(5-O-4,4'-dimethoxytrityl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate
  参考文献：
  名称：

  新型C4连接的咪唑核糖核苷亚磷酰胺的合成，用于探测核酶中的总酸和碱催化

  摘要：

  我们描述了新型C4连接的咪唑核糖核苷亚磷酰胺（PA）1a的合成，通过该合成，咪唑部分被掺入VS核酶中，以研究其在一般酸和碱催化中的作用。对咪唑-N保护基的研究首先表明，新戊酰氧基甲基（POM）作为咪唑核苷的N-保护基是足够的，在温和的碱性条件下可以很容易地将其除去。此外，合成方法扩展到2'-脱氧-和2'- O-烯丙基核苷PA 1b和1c的合成。

  DOI：

  10.1016/j.tet.2005.09.063

文献信息

• Synthesis of novel C4-linked imidazole ribonucleoside phosphoramidites for probing general acid and base catalysis in ribozyme
  作者：Lisa Araki、Shinya Harusawa、Maho Yamaguchi、Sumi Yonezawa、Natsumi Taniguchi、David M.J. Lilley、Zheng-yun Zhao、Takushi Kurihara

  DOI：10.1016/j.tet.2005.09.063

  日期：2005.12

  We describe the synthesis of novel C4-linked imidazole ribonucleoside phosphoramidite (PA) 1a by which the imidazole moiety is incorporated into VS ribozyme to study its role in general acid and base catalysis. Investigation of protecting groups for the imidazole-N first indicated that pivaloyloxymethyl (POM) was adequate as an N-protecting group for the imidazole nucleoside, which could be readily

  我们描述了新型C4连接的咪唑核糖核苷亚磷酰胺（PA）1a的合成，通过该合成，咪唑部分被掺入VS核酶中，以研究其在一般酸和碱催化中的作用。对咪唑-N保护基的研究首先表明，新戊酰氧基甲基（POM）作为咪唑核苷的N-保护基是足够的，在温和的碱性条件下可以很容易地将其除去。此外，合成方法扩展到2'-脱氧-和2'- O-烯丙基核苷PA 1b和1c的合成。
• Synthesis of C4-linked imidazole ribonucleoside phosphoramidite with pivaloyloxymethyl (POM) group
  作者：Lisa Araki、Shinya Harusawa、Maho Yamaguchi、Sumi Yonezawa、Natsumi Taniguchi、David M.J. Lilley、Zheng-yun Zhao、Takushi Kurihara

  DOI：10.1016/j.tetlet.2004.01.132

  日期：2004.3

  A novel C4-linked imidazole ribonucleoside phosphoramidite was designed and successfully synthesized starting from tribenzylribofuranosylimidazole. This phosphoramidite product enables incorporation of the imidazole moiety into an RNA sequence and hence allows study of its role in the general acid and base catalysis of ribozymes. Pivaloyloxymethyl (POM) was first introduced as an N-protecting group

  设计了一种新型的C4连接的咪唑核糖核苷亚磷酰胺，并成功地从三苄基核呋喃呋喃基咪唑开始合成。该亚磷酰胺产品能够将咪唑部分掺入RNA序列，因此可以研究其在核糖酶的一般酸和碱催化中的作用。首先引入新戊酰氧基甲基（POM）作为咪唑核糖核苷的N保护基，该保护基在温和的碱性条件下可以轻松除去。
• Efficient Synthesis of 2’-O-Cyanoethylated Imidazole C-Ribonucleoside Phosphoramidite: A Practical Building Block for Probing the Catalytic Mechanism of Ribozymes
  作者：Shinya Harusawa、Lisa Araki、Zheng-yun Zhao、David M. J. Lilley

  DOI：10.3987/com-10-11978

  日期：——

  A high-yielding synthetic route leading to new 2'-O-cyanoethylated imidazole C-ribonucleoside phosphoramidite (PA) 1 has been developed (41% overall yield in ten steps). This has resulted in a marked improvement of yield compared to unstable 2'-O-TBDMS PA 2. The new synthon PA 1 enables the imidazole moiety to be incorporated into any RNA sequence in principle, and has been used as a practical building block for probing the catalytic mechanism of a ribozyme.