5'-O-(dimethoxytrityl)thymidine 3'-O-methylphosphonofluoridate | 174955-63-6

• 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: 5'-O-(dimethoxytrityl)thymidine 3'-O-methylphosphonofluoridate
• 英文别名: 5'-O-DMT-thymidine 3'-O-methanephosphonofluoridate；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[fluoro(methyl)phosphoryl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 174955-63-6
• 化学式: C₃₂H₃₄FN₂O₈P
• 分子量: 624.603
• InChiKey: OUCPODMGBLARBA-VBALQNMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-N2-isobutyryl-2'-deoxyguanosine 、 5'-O-(dimethoxytrityl)thymidine 3'-O-methylphosphonofluoridate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
  参考文献：
  名称：

  New Approach to the Synthesis of Oligo(nucleoside methanephosphonate)s¹

  摘要：

  new method of preparation of 5'-O-DMT-(N-protected) nucleoside 3'-O-(methanephosphonofluoridates) 2 and their phosphonylating properties toward alcohols, in particular the 5'-hydroxyl groups of nucleosides (or nucleotides), is presented. Preparation of dinucleoside (3',5')-methanephosphonates 3 in solution and solid-phase synthesis of Me-Oligo 6 demonstrate the potential use of 2 as monomers.

  DOI：

  10.1021/jo951333v
• 作为产物：
  描述：

  (Rp)-5'-O-DMT-thymidine-3'-O-(Se-methyl methanephosphonoselenolate) 在 silver fluoride 作用下， 以 水 、 乙腈 为溶剂， 反应 0.08h， 以96%的产率得到5'-O-(dimethoxytrityl)thymidine 3'-O-methylphosphonofluoridate
  参考文献：
  名称：

  New Approach to the Synthesis of Oligo(nucleoside methanephosphonate)s¹

  摘要：

  new method of preparation of 5'-O-DMT-(N-protected) nucleoside 3'-O-(methanephosphonofluoridates) 2 and their phosphonylating properties toward alcohols, in particular the 5'-hydroxyl groups of nucleosides (or nucleotides), is presented. Preparation of dinucleoside (3',5')-methanephosphonates 3 in solution and solid-phase synthesis of Me-Oligo 6 demonstrate the potential use of 2 as monomers.

  DOI：

  10.1021/jo951333v

文献信息

• Nucleoside 3'-methylphosphonofluoridates and nucleoside 3'-methylfluorido-phosphonothioates. New convenient intermediates in large scale synthesis of dinucleoside-(3',5')-methylphosphonates
  作者：Wojciech Dabkowski、Izabela Tworowska、Roustem Saiakhov

  DOI：10.1016/0040-4039(95)01946-f

  日期：1995.12

  Nucleoside 3'-methylphosphonofluoridates 3 and nucleoside 3'-methylfluoridophosphonothioates 5 for the first time are used directly in the synthesis of dinucleosidemethylphosphonates and methylphosphonothioates. The fluoridophosphonothioates 5 were separated into pure diastereomers.

  首次将核苷3'-甲基氟代膦酸酯3和核苷3'-甲基氟代硫代磷酸酯5直接用于合成二核苷甲基代膦酸酯和甲基硫代膦酸酯。氟代硫代磷酸膦酸酯5被分离成纯的非对映异构体。
• Preparation of Thymine Dinucleotide Methylphosphonate Analogs via Thymine Methylphosphonofluoridate
  作者：Michael C. Pirrung、N. Chidambaram

  DOI：10.1021/jo951395l

  日期：1996.1.1
• New Approach to the Synthesis of Oligo(nucleoside methanephosphonate)s¹
  作者：Lucyna Woźniak、Jarosław Pyzowski、Wojciech J. Stec

  DOI：10.1021/jo951333v

  日期：1996.1.1

  new method of preparation of 5'-O-DMT-(N-protected) nucleoside 3'-O-(methanephosphonofluoridates) 2 and their phosphonylating properties toward alcohols, in particular the 5'-hydroxyl groups of nucleosides (or nucleotides), is presented. Preparation of dinucleoside (3',5')-methanephosphonates 3 in solution and solid-phase synthesis of Me-Oligo 6 demonstrate the potential use of 2 as monomers.