tert-butyl 2-[(2R,3R,4R,5R)-2-(2,4-dioxo-3-tritylsulfanylpyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetate | 156703-89-8

• 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: tert-butyl 2-[(2R,3R,4R,5R)-2-(2,4-dioxo-3-tritylsulfanylpyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetate
• CAS: 156703-89-8
• 化学式: C₃₄H₃₆N₂O₈S
• 分子量: 632.734
• InChiKey: XOJGYZVUDAMICW-VNWIGOPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  129.22
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(2R,3R,4R,5R)-2-(2,4-dioxo-3-tritylsulfanylpyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetate 在 咪唑 、 四氮唑 、 氢氧化钾 、 N-羟基丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 氨苯砜 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.58h， 生成 N-[[1-[(3aR,4R,6R,6aR)-6-[bis(phenylsulfanyl)phosphoryloxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,4-dioxopyrimidin-5-yl]methyl]-2-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyacetamide
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o
• 作为产物：
  描述：

  N³-[(triphenylmethyl)sulfenyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 tert-butyl 2-[(2R,3R,4R,5R)-2-(2,4-dioxo-3-tritylsulfanylpyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyacetate
  参考文献：
  名称：

  Sekine; Seio; Wada, Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4469 - 4470

  摘要：

  DOI：