2-fluoro-O⁶-benzyl-2'-deoxyinosine | 144640-76-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-fluoro-O⁶-benzyl-2'-deoxyinosine
• 英文别名: O⁶-benzyl-2-fluoro-2'-deoxyinosine；(2R,3S,5R)-5-(2-fluoro-6-phenylmethoxypurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 144640-76-6
• 化学式: C₁₇H₁₇FN₄O₄
• 分子量: 360.345
• InChiKey: LANALGLGMFDWIU-YNEHKIRRSA-N

物化性质

• 沸点：
  683.0±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-fluoro-O⁶-benzyl-2'-deoxyinosine 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 lithium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 2-fluoro-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyinosine
  参考文献：
  名称：

  A Rapid, High-Yield Method for 5′-Hydroxyl Protection in Very Reactive and Amino Group Modified Nucleosides Using Dimethoxytrityl Tetrafluoroborate

  摘要：

  The conventional method for 4,4'-dimethoxytrityl (DMT) etherification of the 5'-hydroxyl termini in deoxynucleosides that are either highly reactive or those bearing modifications at the exocyclic amino group can be quite problematic, and in several cases the yields are at best mediocre. Herein, we report a rapid, convenient and general procedure for the facile 5'-hydroxyl protection of these nucleosides in exceptionally high yields using DM(+)BF(4)(.). This reagent is particularly useful for the preparation of 5'-O-DMT ethers of nucleosides that are either synthetically valuable or for those that undergo degradation under standard conditions.

  DOI：

  10.1080/07328319608002032
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 4-二甲氨基吡啶 、 氨 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 0.91h， 生成 2-fluoro-O⁶-benzyl-2'-deoxyinosine
  参考文献：
  名称：

  Epoxide and diol epoxide adducts of polycyclic aromatic hydrocarbons at the exocyclic amino group of deoxyguanosine

  摘要：

  Synthesis and separation of the diastereomeric trans N2-2'-deoxyguanosine adducts of tetrahydrophenanthrene 3,4-epoxide and benzo[a]pyrene 7,8-diol 9, 10-epoxide (benzylic hydroxyl group and epoxide oxygen trans), as well as the incorporation of the former into the pentanucleotide TpApG*pApT, are described.

  DOI：

  10.1016/s0040-4039(00)92649-2

文献信息

• A Robust Synthetic Route to 2‘-Deoxy-3‘-nucleotide Derivatives of Modified Nucleobases
  作者：C. M. Prusiewicz、R. Sangaiah、K. B. Tomer、A. Gold

  DOI：10.1021/jo982473i

  日期：1999.10.1
• Epoxide and diol epoxide adducts of polycyclic aromatic hydrocarbons at the exocyclic amino group of deoxyguanosine
  作者：Barbara Zajc、Mahesh K. Lakshman、Jane M. Sayer、Donald M. Jerina

  DOI：10.1016/s0040-4039(00)92649-2

  日期：1992.6

  Synthesis and separation of the diastereomeric trans N2-2'-deoxyguanosine adducts of tetrahydrophenanthrene 3,4-epoxide and benzo[a]pyrene 7,8-diol 9, 10-epoxide (benzylic hydroxyl group and epoxide oxygen trans), as well as the incorporation of the former into the pentanucleotide TpApG*pApT, are described.
• A Rapid, High-Yield Method for 5′-Hydroxyl Protection in Very Reactive and Amino Group Modified Nucleosides Using Dimethoxytrityl Tetrafluoroborate
  作者：Mahesh K. Lakshman、Barbara Zajc

  DOI：10.1080/07328319608002032

  日期：1996.5

  The conventional method for 4,4'-dimethoxytrityl (DMT) etherification of the 5'-hydroxyl termini in deoxynucleosides that are either highly reactive or those bearing modifications at the exocyclic amino group can be quite problematic, and in several cases the yields are at best mediocre. Herein, we report a rapid, convenient and general procedure for the facile 5'-hydroxyl protection of these nucleosides in exceptionally high yields using DM(+)BF(4)(.). This reagent is particularly useful for the preparation of 5'-O-DMT ethers of nucleosides that are either synthetically valuable or for those that undergo degradation under standard conditions.