1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 607716-75-6

• 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-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-ethenyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 607716-75-6
• 化学式: C₂₄H₄₄N₂O₅Si₂
• 分子量: 496.795
• InChiKey: ZQZKQUPKDKXVNI-XLNZFTOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 四氮唑 、 叔丁基过氧化氢 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 3-[[(1S)-1-[(2S,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]but-3-enoxy]-[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-ethenyl-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-oxidophosphaniumyl]oxypropanenitrile
  参考文献：
  名称：

  Dinucleotides of 4′-C-vinyl- and 5′-C-allylthymidine as substrates for ring-closing metathesis reactions

  摘要：

  Thymidine derivatives containing a 4'-C-vinyl group or a 5'-C-allyl group are synthesized and used as building blocks for three different dinucleotides. These are evaluated as substrates for ring-closing metathesis cyclisations, and a protected 5'-C-allylthymidine homo-dimer is found to be the most reactive. A protected precursor for a conformationally restricted cyclic dinucleotide with a four carbon 5'-C to 5'-C connection is hereby efficiently obtained, whereas a corresponding three carbon 4'-C to 5'-C connection is obtained in a lower yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01584-3
• 作为产物：
  描述：

  甲基三苯基溴化膦 、 (2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5-vinyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Dinucleotides of 4′-C-vinyl- and 5′-C-allylthymidine as substrates for ring-closing metathesis reactions

  摘要：

  Thymidine derivatives containing a 4'-C-vinyl group or a 5'-C-allyl group are synthesized and used as building blocks for three different dinucleotides. These are evaluated as substrates for ring-closing metathesis cyclisations, and a protected 5'-C-allylthymidine homo-dimer is found to be the most reactive. A protected precursor for a conformationally restricted cyclic dinucleotide with a four carbon 5'-C to 5'-C connection is hereby efficiently obtained, whereas a corresponding three carbon 4'-C to 5'-C connection is obtained in a lower yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01584-3