3'-O-acetyl-5'-O-triphenylmethylthymidine | 23583-46-2

• 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-5'-O-triphenylmethylthymidine
• 英文别名: 3'-O-acetyl-5'-O-trityl thymidine；3'-O-acetyl-5'-O-trityl-thymidine；O^3'-acetyl-O^5'-trityl-thymidine；O^3'-Acetyl-O^5'-trityl-thymidin
• CAS: 23583-46-2
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: DEGATORPQLZNGR-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5'-O-triphenylmethylthymidine 在 吡啶 、 sodium hydroxide 、 四丁基溴化铵 、 水 、 sodium methylate 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 68.5h， 生成 9-benzyl-2-[N3-benzyl-5-methyl-2,4(1H,3H)-pyrimidinedion-1-yl]-perhydro-6,8-(epoxyimino)furo[3,2-b]oxepin
  参考文献：
  名称：

  An entry to unusual classes of nucleoside analogues

  摘要：

  Nucleosides 6a, 6b and 16-18 having additional carbocycle or oxygen heterocycle fused to the ribose moiety have been synthesized by two routes. While 6a and 6b could be obtained from thymidine using 1, 3-dipolar cycloaddition approach, Vorbruggen reaction on appropriate preformed carbocyclic derivatives furnished 16-18. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00141-5
• 作为产物：
  描述：

  三苯基氯甲烷 在 吡啶 作用下， 生成 3'-O-acetyl-5'-O-triphenylmethylthymidine
  参考文献：
  名称：

  198.核苷酸。第XX部分。源自胸苷的单核苷酸。天然胸苷酸与5'-胸苷磷酸的鉴定

  摘要：

  DOI：

  10.1039/jr9530000951

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 and evaluation of mimetics of UDP and UDP-α-<scp>d</scp>-galactose, dTDP and dTDP-α-<scp>d</scp>-glucose with monosaccharides replacing the key pyrophosphate unit
  作者：Lluis Ballell、Robert J. Young、Robert A. Field

  DOI：10.1039/b500418g

  日期：——

  A series of 5′-O-glycosyl-uridine and thymidine derivatives have been prepared as potential mimics of sugar nucelotides and nucleotide-diphosphates. These compounds proved not to be inhibitors of bovine β-1,4-galactosyltransferase although some showed moderate inhibition of Salmonella dTDP-α-D-glucose 4,6-dehydratase (RmlB).

  一系列5′-O-糖苷尿苷和胸苷衍生物已被制备为潜在的糖核苷酸和核苷二磷酸的模拟物。这些化合物未能抑制牛β-1,4-半乳糖基转移酶，尽管有些对沙门氏菌dTDP-α-D-葡萄糖4,6-脱水酶（RmlB）表现出中等抑制作用。
• Exploring the potential of 3′-O-carboxy esters of thymidine as inhibitors of ribonuclease A and angiogenin
  作者：Kalyan S. Ghosh、Joy Debnath、Palash Dutta、Bijaya K. Sahoo、Swagata Dasgupta

  DOI：10.1016/j.bmc.2008.01.003

  日期：2008.3.15

  In this study, compounds with a carboxy ester in lieu of the phosphate ester at the 3'-position have been employed to inhibit the ribonucleolytic activity of ribonuclease A (RNase A). Phosphates at the 3'-position of pyrimidine bases are well-known inhibitors of the protein. We have investigated the inhibition of RNase A by 3'-O-carboxy esters of thymidine. The compounds behave as competitive inhibitors with inhibition constants ranging from 42 to 95 mu M. The mode of inhibition has also been confirmed by H-1 NMR studies of the active site histidines of RNase A. Docking studies have further substantiated the experimental results. The compounds are also found to inhibit the ribonucleolytic activity of angiogenin, a homologous protein and potent inducer of blood vessel formation. (C) 2008 Elsevier Ltd. All rights reserved.