5'-O-(4,4'-dimethoxytrityl)thimidin-3'-yl phosphate

• 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-(4,4'-dimethoxytrityl)thimidin-3'-yl phosphate
• 英文别名: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] phosphate
• 化学式: C₃₁H₃₁N₂O₁₀P
• 分子量: 622.568
• InChiKey: HNOIRRQNQMOBMJ-UPRLRBBYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] bis(trimethylsilyl) phosphite 在 水 、 碘 作用下， 以 吡啶 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)thimidin-3'-yl phosphate
  参考文献：
  名称：

  Garegg, Per J.; Regberg, Tor; Stawinski, Jacek, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1269 - 1274

  摘要：

  DOI：

文献信息

• Optimization and Mechanistic Analysis of Oligonucleotide Cleavage from Palladium-Labile Solid-Phase Synthesis Supports¹
  作者：Marc M. Greenberg、Tracy J. Matray、Jeffrey D. Kahl、Dong Jin Yoo、Dustin L. McMinn

  DOI：10.1021/jo980135b

  日期：1998.6.1

  Pd(0)-labile solid-phase synthesis supports have been used to produce oligonucleotides containing S'-alkyl carboxylic acid and 3'-hydroxy termini in quantitative yields. Optimization of the cleavage reaction conditions using tetrabutylammonium formate buffer resulted in quantitative yields of oligonucleotides using 4 molar equiv of Pd-2(dba)(3).CHCl3 in 1 h at 55 degrees C. A proton source facilitates cleavage of the oligonucleotide from the supports. Trace amounts of water, acting as a nucleophile on the eta(3)-complex, presumably preventing back biting by the initially released oligonucleotide, are required to obtain reproducibly high yields of cleaved oligonucleotides during a 1 h reaction. The previously observed lability of beta-cyanoethyl groups to the Pd(0) conditions has been examined using a mononucleotide substrate. Cleavage of the beta-cyanoethyl group was shown to proceed to the exclusion of other alkyl groups. A mechanism involving initial insertion by Pd(0) into the carbon-oxygen bond of the beta-cyanoethyl group is suggested to account for the cleavage of this group.
• Garegg, Per J.; Regberg, Tor; Stawinski, Jacek, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1269 - 1274
  作者：Garegg, Per J.、Regberg, Tor、Stawinski, Jacek、Stroemberg, Roger

  DOI：——

  日期：——