5'-O-trityl-3'-O-tert-butyldimethylsilyl thymidine | 213552-25-1

• 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-trityl-3'-O-tert-butyldimethylsilyl thymidine
• 英文别名: TBDMS(-3)[Trt(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 213552-25-1
• 化学式: C₃₅H₄₂N₂O₅Si
• 分子量: 598.814
• InChiKey: UOOTXBZBURNHSL-OJDZSJEKSA-N

物化性质

• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.53
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-O-trityl-3'-O-tert-butyldimethylsilyl thymidine 在 甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde
  参考文献：
  名称：

  Synthesis of novel carbazoyl linked pyrimidine-pyrimidine and pyrimidine-purine dinucleotide analogues

  摘要：

  The synthesis of two backbone modified dinucleotide analogues is described in which the natural phosphodiester linkage is replaced by a 3'-5' carbazoyl linkage. In both cases the bridge was formed through a coupling reaction between an appropriate 3'-carbazoyl nucleoside analogue and an aldehyde nucleoside derivative. It is noteworthy that starting nucleosides 4 could be common materials to obtain the 3'-carbazoyl nucleoside derivatives 2, by means of a simple, previously-described chemoenzymatic procedure, and the aldehyde nucleoside 3, by an oxidation reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00009-x
• 作为产物：
  描述：

  beta-胸苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5'-O-trityl-3'-O-tert-butyldimethylsilyl thymidine
  参考文献：
  名称：

  5-氟-2'-脱氧尿苷氨基磷酸酯类似物的合成和生物学评估。

  摘要：

  已经制备了一系列5-氟-2'-脱氧尿苷的烷基化氨基磷酸酯类似物，并在体外评估了它们对鼠L1210白血病和B16黑素瘤细胞的生长抑制活性。这些化合物被设计为可在胞内释放氨基磷酸酯阴离子，希望它们可作为胸苷酸合酶的不可逆抑制剂起作用。期望的是核苷部分的结合将随后经由氨基磷酸酯使酶烷基化。氯化物，溴化物，碘化物和甲苯磺酸酯类似物是L1210细胞增殖的高效抑制剂，在较高的药物浓度和较长的暴露时间下均观察到抑制作用增强。胸苷的添加完全逆转了所有化合物的抑制作用，提示这些化合物通过抑制胸苷酸合酶起作用。尽管非烷基化吗啉类似物1f为约。哌啶类似物1g的效力比甲基（氯乙基）氨基化合物低50倍，效力仅低2倍，这证明氮的碱性与烷基化基团的存在同样重要。胸苷的添加逆转了吗啉和哌啶类似物的生长抑制，表明这些化合物也可能经历细胞内转化为5-氟-2'-脱氧尿苷5'单磷酸酯。胸苷和脱氧尿苷衍生物2和3在L1210分析中

  DOI：

  10.1021/jm00014a019

文献信息

• Organocatalytic Conversion of Nucleosides to Furanoid Glycals
  作者：Edna Mao、Cheol K. Chung、Yining Ji、Yu-hong Lam、Peter E. Maligres

  DOI：10.1021/acs.joc.1c00555

  日期：2021.6.4

  2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides allowing the elimination of the nucleobase giving the corresponding glycal. These mild conditions were demonstrated in the syntheses of glycals with various substitution patterns while minimizing the formation of undesired byproducts

  已经发现了一类对将 2'-脱氧核苷转化为呋喃糖苷具有高活性的有机催化剂。这些磷酰亚胺(Ph 2 PS) 2 NH 和 (Ph 2 PSe) 2 NH 显示出可有效介导 2'-脱氧核苷的全甲硅烷基化，从而消除核碱基，产生相应的糖基。这些温和的条件在具有各种取代模式的糖醛的合成中得到了证明，同时最大限度地减少了不需要的副产物的形成并扩大了该方法的范围。
• Efficient Desilylation of some Nucleoside Derivatives with Potassium<i>tert</i>-Butoxide in Dimethylformamide
  作者：G. Negrón、F. Vásquezy、G. Calderón、R. Cruz、R. Gaviño、G. Islas

  DOI：10.1080/00397919808004881

  日期：1998.8

  A new method for deprotecting silyl ethers of nucleosides has been established by using potassium tert-butoxide in dimethylformamide at room temperature.
• Comparative inhibitory activity of 3′- and 5′-functionalized nucleosides on ribonuclease A
  作者：Joy Debnath、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2010.10.005

  日期：2010.12

  Modified nucleosides, molecules, functionalized with various polar groups at different positions have been synthesized to rationalize the impact of structural modification on their inhibitory activity. Agarose gel and precipitation assays indicate their improved inhibitory activity on ribonuclease A (RNase A). Kinetic experiments clearly categorize them as competitive inhibitors of RNase A with improved inhibition constant (K-i) values (37 +/- 9, 67 +/- 6, and 193 +/- 7 mu M for compounds 10, 3, and 7, respectively). The preferential hydrogen bonding network formation between His-12 and His-119 of RNase A with the polar carboxylic and amino groups of these compounds has been evidenced from the docking studies. The relationship between structural modifications and inhibitory activity of these compounds is further justified in terms of energetics using PEARLS. (C) 2010 Elsevier Ltd. All rights reserved.