1-[(6aR,8R,9R,9aS)-9-(hydroxymethyl)-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]pyrimidine-2,4-dione | 199480-48-3

• 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: 1-[(6aR,8R,9R,9aS)-9-(hydroxymethyl)-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]pyrimidine-2,4-dione
• CAS: 199480-48-3
• 化学式: C₂₂H₄₀N₂O₇Si₂
• 分子量: 500.74
• InChiKey: NYWAAMJZPLFRPX-RMVXJAJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(6aR,8R,9R,9aS)-9-(hydroxymethyl)-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]pyrimidine-2,4-dione 在 吡啶 、 四氮唑 、 氢氟酸 、 氨 、 碘 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 3-[[(4aR,5R,7R,7aS)-7-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dioxopyrimidin-1-yl)-2-oxo-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3,2]dioxaphosphinin-2-yl]oxy]propanenitrile
  参考文献：
  名称：

  The synthesis of a novel 2′,3′-cyclic phosphate derived from 2′-homouridine

  摘要：

  The novel 2',3'-cyclic phosphate (1) derived from 2'-homouridine has been prepared by phosphorylation with 2-cyanocthyl N,N,N',N' -tetrapropylphosphorodiamidite. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01952-2
• 作为产物：
  描述：

  1-((2R,3R,3aS,9aR)-3-Allyl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-4-hydroxy-1H-pyrimidin-2-one 在 sodium tetrahydroborate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 生成 1-[(6aR,8R,9R,9aS)-9-(hydroxymethyl)-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]pyrimidine-2,4-dione
  参考文献：
  名称：

  The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA

  摘要：

  Five 2'-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed.

  DOI：

  10.1080/07328319708006215

文献信息

• Synthesis of Nucleosides with Additional Nucleobases
  作者：Charlotte Andersen、S⊘ren L. Pedersen、Poul Nielsen

  DOI：10.1080/15257770701542199

  日期：2007.11.26

  The syntheses of two nucleosides with additional nucleobases in the 2'-position are presented. The nucleosides have two- and one-carbon linkers to the additional nucleobase, respectively. The two nucleosides are synthesized from different strategies. The nucleoside with two carbons in the linker has been incorporated into oligonucleotides and showed stabilization of a tree-way junction.

  提出了两个在2'位置具有附加核苷碱基的核苷的合成。核苷分别具有至另一个核苷碱基的二碳和一碳接头。这两种核苷是从不同的策略合成的。连接子中具有两个碳原子的核苷已被整合到寡核苷酸中，并显示出树状连接的稳定性。
• Synthesis and transcription studies on 5′-triphosphates derived from 2′-C-branched-uridines: 2′-homouridine-5′-triphosphate is a substrate for T7 RNA polymerase
  作者：John B. J. Pavey、Anthony J. Lawrence、Ian A. O'Neil、Stefan Vortler、Richard Cosstick

  DOI：10.1039/b314348a

  日期：——

  The 5'-triphosphates of 2'-hydroxymethyluridine (2'-homouridine) and 2'-hydroxyethyluridine were prepared from the corresponding acetyl-protected nucleosides by initial phosphitylation with 2-chloro-5,6-benzo-1,2,3-dioxaphosphorin-4-one. 2'-Acetamidouridine 5'-triphosphate was prepared in an analogous fashion from uridine 2'-C-, 3'-O-gamma-butyrolactone, in which the 3'-hydroxyl group is internally

  2'-羟基甲基尿苷（2'-高尿嘧啶）和2'-羟基乙基尿苷的5'-三磷酸酯是由相应的乙酰基保护的核苷通过用2-氯-5,6-苯并-1,2,3-进行的磷酸化作用而制备的。二氧磷磷-4-一。由尿苷2′-C-，3′-O-γ-丁内酯以类似的方式制备2′-乙酰胺基尿苷5′-三磷酸酯，其中3′-羟基在内部被保护为内酯。随后用氨处理得到所需的三磷酸乙酰氨基酯。研究了所有三种三磷酸酯作为T7 RNA聚合酶的底物和该酶的Y639F突变体。2' 发现在甲基锰的存在下，三磷酸合尿苷是野生型酶的底物，并且被特异地掺入到短RNA转录物中（长度为20和21个核苷酸）。通过其对碱水解的抗性证实了转录物中存在类似物。凝胶电泳分析还表明，可以将2'-同型尿苷与长度为75个核苷酸的转录物多重结合。这是2'-脱氧2'-α-C分支的5'-三磷酸核苷充当T7 RNA聚合酶底物的首次报道。2'-羟乙基-和2'-乙酰氨基-尿苷三磷酸不是酶
• The synthesis of 2′-homouridine, its incorporation into a dinucleoside monophosphate and hydrolytic behaviour of the dimer
  作者：John B.J. Pavey、Anthony J. Lawrence、Andrew J. Potter、Richard Cosstick、Ian A. O'Neil

  DOI：10.1016/s0040-4039(98)01478-6

  日期：1998.9

  An efficient route to 2'-homouridine (1), a new nucleoside analogue, is reported that is based on an ene reaction. This nucleoside has been incorporated into a dinucleoside monophosphate and hydrolytic studies on the dimer show that it does not behave like a ribonucleotide. (C) 1998 Elsevier Science Ltd. All rights reserved.