3-[[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridin-4-yl]-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxypropanenitrile | 276679-06-2

• 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: 3-[[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridin-4-yl]-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxypropanenitrile
• CAS: 276679-06-2
• 化学式: C₅₂H₆₅N₆O₁₃PSi
• 分子量: 1041.18
• InChiKey: QBYWDJBBXIBNKN-DVMJEAHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  73
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  217
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3-[[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridin-4-yl]-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxypropanenitrile 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 生成 3-[[(2R,3S,5R)-2-[[[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridin-4-yl]-(2-cyanoethoxy)-oxidophosphaniumyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.

  DOI：

  10.1080/15257770008033851
• 作为产物：
  描述：

  3'-氨基-2',3'-双脱氧胸苷 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 sodium carbonate 、 silver nitrate 、 二甲基亚砜 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 55.0 ℃ 、344.74 kPa 条件下， 反应 88.5h， 生成 3-[[(2R,3aS,7R,7aS)-7-[bis(4-methoxyphenyl)-phenylmethoxy]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyridin-4-yl]-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxypropanenitrile
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.

  DOI：

  10.1080/15257770008033851

文献信息

• Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine
  作者：Guangyi Wang、Vesna Stoisavljevic

  DOI：10.1080/15257770008033851

  日期：2000.9

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.