3'-O-acetyl-2'-deoxy-5'-O-triphenylmethyluridine | 121356-00-1

• 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: 3'-O-acetyl-2'-deoxy-5'-O-triphenylmethyluridine
• 英文别名: O^3'-acetyl-O^5'-trityl-2'-deoxy-uridine；[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-2-(trityloxymethyl)oxolan-3-yl] acetate
• CAS: 121356-00-1
• 化学式: C₃₀H₂₈N₂O₆
• 分子量: 512.562
• InChiKey: VUMZSAAYBNOZCZ-ZRRKCSAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-2'-deoxy-5'-O-triphenylmethyluridine 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氨 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 11.25h， 生成 3-[[(1R,6S,7S,8R,9R,14R,16R,17S,22R,23S)-16-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,5,10,12-tetraoxo-15,18,20,25-tetraoxa-2,4,11,13-tetrazahexacyclo[20.2.1.114,17.02,7.06,9.08,13]hexacosan-23-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Synthesis, Crystal Structure, and Enzymatic Evaluation of a DNA-Photolesion Isostere

  摘要：

  Nucleotide analogues are useful tools for the investigation of interactions between DNA-binding proteins and DNA at a molecular level. Herein we describe the synthesis of the DNA-lesion analogue 2, which is required to determine the extent to which specific phosphodiesters in the DNA backbone contribute to the recognition of cyclobutane pyrimidine dimer DNA lesion by the dimer-specific repair enzymes DNA photolyases or T4-endonuclease V. The analogue 2 is a close structural mimic of cyclobutane pyrimidine dimers like 1. which are the major lesions induced upon irradiation of cells with UV light. Instead of the negatively charged phosphate link in 1, analogue 2 contains an uncharged but isosteric formacetal moiety. The analysis of this and other phosphodiester contacts is hoped to provide insight into the lesion recognition process, which is currently believed to require the nipping of the lesioned base out of the DNA double helix. The lesion analogue 2 is synthetically available in large quantities, which allowed us to establish a new, fast and sensitive DNA photolyase assay. A precise X-ray crystal structure analysis of the DNA-lesion analogue 2 is also presented. The structure underlines the isosteric character of 2 and reveals, in combination with the only other available X-ray crystal structure determined from a thymine-dimer triester analogue, interesting structural features of cyclobutane pyrimidine dimer lesions. We describe the incorporation of the lesion analogue 2 into oligonucleotides by using standard phosphoramidite chemistry. Initial enzymatic repair studies are reported with three different types of DNA photolyases. These studies show that the lesion analogue 2 is rapidly repaired by photolyases from Anacystis nidulans, Neurospora crassa and from the marsupial Potorous tridactylis. The enzymatic investigations indicate that all photolyases, including enzymes from higher organisms (Tridactylis) accept the formacetal dimer as a lesion substrate and therefore could possess a similar DNA-lesion recognition process, in which the interaction with the central phosphate unit is only of limited importance.

  DOI：

  10.1002/(sici)1521-3765(19980416)4:4<642::aid-chem642>3.0.co;2-k
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-chloro-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以96%的产率得到3'-O-acetyl-2'-deoxy-5'-O-triphenylmethyluridine
  参考文献：
  名称：

  不饱和核苷，碳水化合物和其他烯烃的区域特异性合成

  摘要：

  具有一对自由基离去基团（例如氯，溴，苯氧基硫代羰基氧基和咪唑基硫代羰基氧基）的邻位二取代核苷，碳水化合物和环己烷衍生物已成功地以高收率（60-90％）成功转化为相应的烯烃，没有观察到副产物，通过在适当的溶剂中与氢化三正丁基锡和偶氮二异丁腈反应。

  DOI：

  10.1016/s0040-4039(00)97480-x

文献信息

• Protecting Groups Transfer: Unusual Method of Removal of Tr and Tbdms Groups by Transetherification
  作者：Nadia L. D. Cabral、Luciano J. Hoeltgebaum Thiessen、Bogdan Doboszewski

  DOI：10.1080/15257770802257846

  日期：2008.8.11

  The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5′-O-Tr-2′-deoxynucleosides in a process mediated by anhydrous sulfates of Cu+2, Fe+2, or Ni+2 to yield mixtures of 3′,5′-bis-O-Tr and 3′-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl

  在由Cu + 2，Fe + 2或Ni + 2的无水硫酸盐介导的过程中，三苯甲基（Tr）基团在5'-O-Tr-2'-脱氧核苷分子之间进行转移（转移醚化或歧化）得到3′，5′-双-O-Tr和3′-O-Tr产物的混合物。如果反应介质中存在苯甲醇，则会导致脱三苯甲基化并同时形成苯甲基三苯甲基醚。5'-O-TBDMS-2'-脱氧核苷中叔丁基二甲基甲硅烷基（TBDMS）的行为完全相同。以前没有在O-Tr和O-TBDMS组中观察到这种类型的转醚化作用。
• Synthesis of analogues of the O-β-d-Ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY
  作者：C. Dini、N. Drochon、J.C. Guillot、P. Mauvais、P. Walter、J. Aszodi

  DOI：10.1016/s0960-894x(00)00714-9

  日期：2001.2

  O-beta -D-Ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins that maintains enzyme inhibitory activity on MraY. A set of compounds with hydroxyl patterns different from I has been synthesized. The presence of a hydroxyl group in the 3 " position is essential for the activity. The 3'-deoxy derivative (IV), however, shows a 5-fold improved potency. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Detritylation of Ethers Using Iodine−Alcohol Reagents:  An Acid-Catalyzed Reaction
  作者：Jan L. Wahlstrom、Robert C. Ronald

  DOI：10.1021/jo972222u

  日期：1998.8.1