1-[2-O,2'-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine | 869347-10-4

• 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-[2-O,2'-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine
• 英文别名: (1S,2S,9R,11R)-14-methyl-4,4,6,6-tetra(propan-2-yl)-3,5,7,18-tetraoxa-10-thia-12,16-diaza-4,6-disilatetracyclo[9.7.0.02,9.012,17]octadeca-13,16-dien-15-one
• CAS: 869347-10-4
• 化学式: C₂₂H₃₈N₂O₅SSi₂
• 分子量: 498.791
• InChiKey: LAXUFCPYCNUGNZ-WERVVEIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-O,2'-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 在 偶氮二甲氧基异庚腈 、 三氟化硼乙醚 、 四丁基氟化铵 、 三正丁基氢锡 、 溶剂黄146 、 lithium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢噻吩-2-基]-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA

  摘要：

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.

  DOI：

  10.1021/jo051248f
• 作为产物：
  描述：

  胸腺嘧啶 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 、 甲胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.17h， 生成 1-[2-O,2'-anhydro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA

  摘要：

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.

  DOI：

  10.1021/jo051248f

文献信息

• Practical Synthesis of 2‘-Deoxy-4‘-thioribonucleosides:  Substrates for the Synthesis of 4‘-ThioDNA
  作者：Naonori Inoue、Daisuke Kaga、Noriaki Minakawa、Akira Matsuda

  DOI：10.1021/jo051248f

  日期：2005.10.1

  [GRAPHIC]We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-Deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-Deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.