5'-O-trityl 3-N-benzoylthymidine | 123884-03-7

• 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-N-benzoylthymidine
• 英文别名: 3-benzoyl-1-[(2R,4S,5R)-4-hydroxy-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 123884-03-7
• 化学式: C₃₆H₃₂N₂O₆
• 分子量: 588.66
• InChiKey: FEDQLMVRGNNLTQ-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-trityl 3-N-benzoylthymidine 在 sodium hydride 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 27.0h， 生成 3'-deoxy-3'-O-[(carboxymethyl)oxo]thymidine
  参考文献：
  名称：

  3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition

  摘要：

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.047
• 作为产物：
  描述：

  N³-benzoyl thymidine 、 三苯基氯甲烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到5'-O-trityl 3-N-benzoylthymidine
  参考文献：
  名称：

  Facile synthesis of 3'-O-methylthymidine and 3'-deoxythymidine and related deoxygenated thymidine derivative: a new method for selective deoxygenation of secondary hydroxy groups

  摘要：

  DOI：

  10.1021/jo00290a024

文献信息

• Facile Chlorination of Sugar Moiety of Nucleosides by Use of Tris(2,4,6-tribromophenoxy)dichlorophosphorane
  作者：Shokichi Ohuchi、Ramendra K. Singh、Takeshi Wada、Tsujiaki Hata

  DOI：10.1246/cl.1992.1505

  日期：1992.8

  A versatile chlorinating reagent, tris(2,4,6-tribromophenoxy)dichlorophosphorane was applied for 5′- and 3′-chlorination of nucleosides. It was found that the reaction proceeded via SN2 mechanism.

  多功能氯化试剂三（2,4,6-三溴苯氧基）二氯正膦用于核苷的 5'- 和 3'-氯化。发现反应通过SN2机制进行。
• Singh, Ramendra K.; Ohuchi, Shokichi; Wada, Takeshi, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 123 - 130
  作者：Singh, Ramendra K.、Ohuchi, Shokichi、Wada, Takeshi、Hata, Tsujiaki

  DOI：——

  日期：——
• SEKINE, MITSUO;NAKANISHI, TAKESHI, J. ORG. CHEM., 55,(1990) N, C. 924-928
  作者：SEKINE, MITSUO、NAKANISHI, TAKESHI

  DOI：——

  日期：——
• Facile synthesis of 3'-O-methylthymidine and 3'-deoxythymidine and related deoxygenated thymidine derivative: a new method for selective deoxygenation of secondary hydroxy groups
  作者：Mitsuo Sekine、Takeshi Nakanishi

  DOI：10.1021/jo00290a024

  日期：1990.2
• 3′-Oxo-, amino-, thio- and sulfone-acetic acid modified thymidines: Effect of increased acidity on ribonuclease A inhibition
  作者：Dhrubajyoti Datta、Anirban Samanta、Swagata Dasgupta、Tanmaya Pathak

  DOI：10.1016/j.bmc.2013.05.047

  日期：2013.8

  A family of 3'-functionalized thymidines carrying XCH2COOH (X = O, NH, S, SO2) groups has been designed as inhibitors of RNase A. This is because it is possible to manipulate the overall acidity of this new class of nucleic 'acids' by changing X from oxygen to the SO2 group in the series. It is also expected that the acyclic nature of the XCH2COOH group would provide enough flexibility to the -COOH group to have maximum interactions with the catalytic subsite P-1 of RNase A. As the -SO2CH2COOH substituted derivative showed better potency partially because of the increased acidity of the -COOH group, the inhibitory properties of both 5'-substituted and 3',5'-disubstituted sulfone acetic acid modified thymidines were investigated. Two -SO2CH2COOH groups were incorporated with the expectation of targeting two phosphate binding sites simultaneously. Thus, 3',5'-dideoxy-3',5'-bis-S-[(carboxymethyl)sulfonyl]thymidine emerged as the best inhibitor in this series with a K-i value of 25 +/- 2 mu M. (C) 2013 Elsevier Ltd. All rights reserved.