Thiophosphoric acid O-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester O'-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl] ester | 77245-13-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: Thiophosphoric acid O-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester O'-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl] ester
• 英文别名: 1-[(2R,3R,4S,5R)-5-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy-sulfanylphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 77245-13-7
• 化学式: C₁₈H₂₃N₄O₁₃PS
• 分子量: 566.439
• InChiKey: QZPKUYPXYHEYMQ-IVQUQKRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  269
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 、 sulfur 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 Thiophosphoric acid O-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester O'-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  Ribonucleotide analogues having novel internucleotide linkages

  摘要：

  DOI：

  10.1016/s0040-4039(00)93674-8

文献信息

• Unprecedented Mild Acid-Catalyzed Desilylation of the 2‘-O-<i>tert</i>-Butyldimethylsilyl Group from Chemically Synthesized Oligoribonucleotide Intermediates <i>via</i> Neighboring Group Participation of the Internucleotidic Phosphate Residue
  作者：Shun-ichi Kawahara、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/ja961959i

  日期：1996.1.1

  Hydrolytic removal of the 2'-tert-butyldimethylsilyl (TBDMS) group from a 2'-O-TBDMS protected UpU dimer [U(2'-Si)pU] (1) (Si = TBDMS) and related derivatives under various acidic conditions was studied in detail. First, desilylation of 1 by use of acetic acid was examined. Consequently, we made the unprecedented discovery that cleavage of the 2'-silyl ether linkage occurred fastest at a very low concentration of acetic acid within the range of 5-10%, depending on the temperature, Formic acid could cleave the silyl ether much faster than acetic acid, but the relationship between the reaction rate and the concentration of acid was different from that of acetic acid. The use of 20-40% formic acid resulted in very effective elimination of the 2'-TBDMS group, Moreover, diluted HCl solution (pH 2.0) could cleave the Si-O bond faster than acetic acid at 30 degrees C. In contrast, the 2'-silyl group of the corresponding methylphosphonate derivative [U(2'-Si)p(Me)U] (3) was much more stable than that of 1. In the case of a diastereomeric mixture of the phosphorothioate dimer [U(2'-Si)psU] (2), a big difference in reaction rate between the Rp- and Sp-diastereomers was observed. These results strongly suggest that neighboring group participation of the 3'-5' phosphorodiester group is involved in the present acid-catalyzed 2'-desilylation. These conditions were successfully applied to the deprotection of the 2'-TBDMS group of an RNA intermediate which was chemically synthesized by the conventional phosphoramidite approach on a CPG gel.
• Ribonucleotide analogues having novel internucleotide linkages
  作者：Mona J. Nemer、Kelvin K. Ogilvie

  DOI：10.1016/s0040-4039(00)93674-8

  日期：1980.1