5'-azido-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxyuridine | 251296-58-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-azido-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxyuridine
• CAS: 251296-58-9
• 化学式: C₂₁H₃₉N₅O₅Si₂
• 分子量: 497.742
• InChiKey: JOOHPNKYELENNC-VDHUWJSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  131.31
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5'-azido-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxyuridine 在 1,3-丙二硫醇 、 氢氧化钾 、 sodium tetrahydroborate 、 1-羟基苯并三唑 、 4-吡咯烷基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  甲壳素合酶抑制剂杂芳基-核苷衍生物的设计，合成和生物学评估。

  摘要：

  我们在这里报告了几丁质合酶糖类似物新模型的设计，合成和生物学评估。这些UDP-GlcNAc模拟物将模仿糖的杂芳基和尿苷结合在一起，并与不同的焦磷酸盐生物等排体相连。该化合物对几丁质合酶显示出弱的抑制活性，并且已经针对多种病原真菌对它们的抗真菌效力进行了测定。

  DOI：

  10.1016/s0960-894x(03)00239-7
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 咪唑 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5'-azido-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxyuridine
  参考文献：
  名称：

  甲壳素合酶抑制剂杂芳基-核苷衍生物的设计，合成和生物学评估。

  摘要：

  我们在这里报告了几丁质合酶糖类似物新模型的设计，合成和生物学评估。这些UDP-GlcNAc模拟物将模仿糖的杂芳基和尿苷结合在一起，并与不同的焦磷酸盐生物等排体相连。该化合物对几丁质合酶显示出弱的抑制活性，并且已经针对多种病原真菌对它们的抗真菌效力进行了测定。

  DOI：

  10.1016/s0960-894x(03)00239-7

文献信息

• Synthesis and use of new C-glycosyl bicyclic lactones
  作者：Arkadiusz Listkowski、Otman Otman、Stéphane Chambert、Yves Queneau

  DOI：10.1016/j.tetlet.2015.07.017

  日期：2015.8

  New C-glycosyl bicyclic lactones have been synthesized in three steps from glycosyl bromides and used as synthons towards C-glycosyl derivatives which can readily be elaborated to 1,2-bisfunctionalized carbohydrate systems. The method was illustrated with several examples of pseudo conjugates prepared from the new C-glycosyl 1,2-fused pyrano-δ-lactonic building blocks, either with groups such as allyl

  从糖基溴化物以三个步骤合成了新的C-糖基双环内酯，并将其用作对C-糖基衍生物的合成子，所述C-糖基衍生物可以容易地制成1，2-双官能化的碳水化合物体系。用新的C-糖基1,2-稠合的吡喃基-δ-内酯结构基团制备的假缀合物的几个例子说明了该方法，这些基团具有诸如烯丙基或炔丙基这样的基团，具有较大的后续反应性，或者具有更精细的部分，从而导致模型糖氨基酸或假核苷酸糖。
• Inhibition of Escherichia coli glycosyltransferase MurG and Mycobacterium tuberculosis Gal transferase by uridine-linked transition state mimics
  作者：Amy E. Trunkfield、Sudagar S. Gurcha、Gurdyal S. Besra、Timothy D.H. Bugg

  DOI：10.1016/j.bmc.2010.02.026

  日期：2010.4

  Glycosyltransferase MurG catalyses the transfer of N-acetyl-D-glucosamine to lipid intermediate I on the bacterial peptidoglycan biosynthesis pathway, and is a target for development of new antibacterial agents. A transition state mimic was designed for MurG, containing a functionalised proline, linked through the alpha-carboxylic acid, via a spacer, to a uridine nucleoside. A set of 15 functionalised prolines were synthesised, using a convergent dipolar cycloaddition reaction, which were coupled via either a glycine, proline, sarcosine, or diester linkage to the 5'-position of uridine. The library of 18 final compounds were tested as inhibitors of Escherichia coli glycosyltransferase MurG. Ten compounds showed inhibition of MurG at 1 mM concentration, the most active with IC50 400 mu M. The library was also tested against Mycobacterium tuberculosis galactosyltransferase GlfT2, and one compound showed effective inhibition at 1 mM concentration. (C) 2010 Elsevier Ltd. All rights reserved.
• Second-generation dimeric inhibitors of chitin synthase
  作者：Adam R. Yeager、Nathaniel S. Finney

  DOI：10.1016/j.bmc.2004.09.027

  日期：2004.12

  Chitin synthase (CS) is essential for fungal cell wall biosynthesis and is an attractive medicinal target. Expanded results from our efforts to develop mechanism based inhibitors of CS are presented here. Specifically, we describe uridine dieters linked by tartrate amides as potential pyrophosphate ninnies. (C) 2004 Elsevier Ltd. All rights reserved.
• Amide-Linked Ribonucleoside Dimers Derived from 5‘-Amino-5‘-deoxy- and 3‘-(Carboxymethyl)-3‘-deoxynucleoside Precursors¹
  作者：Matt A. Peterson、Bradley L. Nilsson、Sanchita Sarker、Bogdan Doboszewski、Weijian Zhang、Morris J. Robins

  DOI：10.1021/jo9908647

  日期：1999.10.1

  Treatment of tert-butyldimethylsilyl (TBDMS) derivatives of 3'-keto(adenosine or uridine) with [(ethoxycarbonyl)methylene]triphenylphosphorane gave exocyclic alkenes that underwent stereoselective hydrogenation to give 3'-deoxy-3'-[(ethoxycarbonyl)methyl](Ado or Urd) analogues. Saponification provided the 3'-(carboxymethyl)-3'-deoxy(Ado and Urd) derivatives 37 and 38. Treatment of 37 or 38 with DCC and 5'-amino-2',3'-bis-O-TBDMS-5'-deoxynucleosides gave the amide-linked dimers (74-82%). Activation of 37 or 38 with 4-nitrophenol/DCC, and direct coupling of the 4-nitrophenyl esters with 5'-amino-5'-deoxy(Ado or Urd) in pyridine also produced amide dimers efficiently (65-70%). Analogous activation of a 5'-O-DMT-protected carboxylate, and its coupling with 5'-amino-5'-deoxy-2'-O-methyladenosine gave the amide dimer in good yield (74%). Coupling (DCC) of a 5'-azido-2'-O-TBDMS-3'-(carboxymethyl)-3', 5'-dideoxyuridine intermediate with 5'-amino-5'-deoxynucleosides gave amide-linked dimers (72-78%) that can serve as masked (azide reduction) 5'-amino dimers for analogous synthesis of extended amide-linked oligomers.