N(4)-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methylthiomethyl)cytidine | 201667-26-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N(4)-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methylthiomethyl)cytidine
• 英文别名: N4-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methylthiomethyl)cytidine；N-[1-[(6aR,8R,9R,9aR)-9-(methylsulfanylmethoxy)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 201667-26-7
• 化学式: C₂₅H₄₅N₃O₇SSi₂
• 分子量: 587.885
• InChiKey: GDHSPRFIWQWBJZ-MSNJVRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N(4)-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methylthiomethyl)cytidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成
  参考文献：
  名称：

  2′-O-Methyl Thiomethyl Modifications in Hammerhead Ribozymes

  摘要：

  The synthesis of all four phosphoramidites of 2'-O-methylthiomethyl ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.

  DOI：

  10.1080/07328319708006114
• 作为产物：
  描述：

  N-乙酰胞嘧啶核苷 在 2,6-二甲基吡啶 、 过氧化苯甲酰 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 生成 N(4)-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-(methylthiomethyl)cytidine
  参考文献：
  名称：

  2′-O-Methyl Thiomethyl Modifications in Hammerhead Ribozymes

  摘要：

  The synthesis of all four phosphoramidites of 2'-O-methylthiomethyl ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.

  DOI：

  10.1080/07328319708006114

文献信息

• [EN] 2'-O-AMINOOXYMETHYL NUCLEOSIDE DERIVATIVES FOR USE IN THE SYNTHESIS AND MODIFICATION OF NUCLEOSIDES, NUCLEOTIDES AND OLIGONUCLEOTIDES<br/>[FR] DÉRIVÉS DE 2'-O-AMINOOXYMÉTHYL NUCLÉOSIDE POUR L'UTILISATION DANS LA SYNTHÈSE ET LA MODIFICATION DE NUCLÉOSIDES, NUCLÉOTIDES ET OLIGONUCLÉOTIDES
  申请人：US HEALTH

  公开号：WO2012138530A1

  公开（公告）日：2012-10-11

  Disclosed are O-protected compounds of the formula (I):wherein B is an optionally protected nucleobase, and R1-R3 are as described herein, a method of preparing such compounds, and a method of preparing oligonucleotides such as RNA starting from such compounds. The O-protected compounds have one or more advantages, for example, the 2'-O-protected compound is stable during the various reaction steps involved in oligonucleotide synthesis; the protecting group can be easily removed after the synthesis of the oligonucleotide, for example, by reaction with tetrabutylammonium fluoride; and/or the O-protected groups do not generate DNA/RNA alkylating side products, which have been reported during removal of 2'-O-(2-cyanoethyl)oxymethyl or 2'-O-[2-(4-tolylsulfonyl)ethoxymethyl groups under similar conditions.

  揭示了公式（I）中的O-保护化合物：其中B是可选择保护的核碱基，R1-R3如本文所述，一种制备这种化合物的方法，以及一种从这种化合物开始制备寡核苷酸（如RNA）的方法。这些O-保护化合物具有一个或多个优点，例如，2'-O-保护化合物在寡核苷酸合成中涉及的各种反应步骤中是稳定的；保护基在寡核苷酸合成后可以轻松去除，例如，通过与四丁基氟化铵反应；和/或O-保护基在类似条件下去除2'-O-(2-氰乙基)氧甲基或2'-O-[2-(4-甲苯磺酰基)乙氧甲基基团时不会产生已报道的DNA/RNA烷基化副产物。
• Permanent or reversible conjugation of 2′-O- or 5′-O-aminooxymethylated nucleosides with functional groups as a convenient and efficient approach to the modification of RNA and DNA sequences
  作者：Jacek Cieślak、Andrzej Grajkowski、Cristina Ausín、Alexei Gapeev、Serge L. Beaucage

  DOI：10.1093/nar/gkr896

  日期：2012.3

  demonstrated by the single or double incorporation of a reversible pyrenylated uridine 2′-conjugate into an RNA sequence, the conjugation of 2′-O-aminooxymethyl ribonucleosides with aldehydes, including those generated from their acetals, provides reversible 2′-O-protected ribonucleosides for potential applications in the solid-phase synthesis of native RNA sequences. The synthesis of a chimeric polyuridylic

  2'- O-氨基氧基甲基核糖核苷是通过在甲醇中用NH 4 F处理而从它们的3',5'-二甲硅烷基化的2'- O-邻苯二甲酰亚胺氧基甲基衍生物制备的。这些新型核糖核苷与 1-芘甲醛的反应导致以 69-82% 的产率有效形成稳定且可逆的核糖核苷 2'-缀合物。实际上，将这些缀合物暴露于 THF 中的0.5 M 四正丁基氟化铵 (TBAF) 会导致它们的亚氨基醚功能裂解，从而产生天然核糖核苷以及无害的腈副产物。相反，5-cholesten-3-one 或丹磺酰氯与 2'- O 的反应-氨基氧甲基尿苷提供永久性尿苷 2'-结合物，在用 TBAF 处理后基本保持完整。或者，5'- O-氨基氧基甲基胸苷通过其3'- O-乙酰丙酰基-5'- O-邻苯二甲酰亚胺氧基甲基前体的肼解制备。5'- O-氨基氧甲基胸苷的芘基化和 5'-偶联物对 TBAF 的敏感性进一步证明了这种核苷在永久性或可逆性修饰 DNA 序列方面的有用性。尽管
• Synthesis of 2′-O-monohaloethoxymethyl-modified RNAs and their duplex formation ability
  作者：Rintaro Iwata Hara、Masayuki Kageyama、Koichiro Arai、Naoki Uchiyama、Takeshi Wada

  DOI：10.1039/c7ra07767j

  日期：——

  synthesized 2′-O-monohaloethoxymethyl-modified RNAs and evaluated their duplex formation ability. The effects of 2-chloroethoxymethyl (MCEM) and 2-fluoroethoxymethyl groups on the RNA/RNA duplex stability was found to depend on both base sequences and halogen atoms. Only the 2′-O-MCEM-rU12/rA12 duplex was found to be significantly more stable than the unmodified duplex. In this study, it is proposed through

  我们合成了2' - O-单卤代乙氧基甲基修饰的RNA，并评估了其双链体形成能力。发现2-氯乙氧基甲基（MCEM）和2-氟乙氧基甲基对RNA / RNA双链体稳定性的影响取决于碱基序列和卤素原子。发现仅2' - O -MCEM-rU 12 / rA 12双链体比未修饰的双链体明显更稳定。在这项研究中，通过UV熔解分析，等温滴定量热法测量和分子力学计算，提出了这种稳定化可能是由于MCEM基团和互补链中核碱基之间相互作用而产生的焓稳定化所致。
• 2′-<i>O</i>-Methyl Thiomethyl Modifications in Hammerhead Ribozymes
  作者：Alexander Karpeisky、Carolyn Gonzalez、Alex B. Burgin、Nassim Usman、Leonid Beigelman

  DOI：10.1080/07328319708006114

  日期：1997.7

  The synthesis of all four phosphoramidites of 2'-O-methylthiomethyl ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.