3'-deoxy-5'-O-triphenylmethylthymidine | 107036-54-4

• 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'-deoxy-5'-O-triphenylmethylthymidine
• 英文别名: 3'-deoxy-5'-O-tritylthymidine；5'-O-trityl-3'-deoxythymidine；5-methyl-1-[(2R,5S)-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 107036-54-4
• 化学式: C₂₉H₂₈N₂O₄
• 分子量: 468.552
• InChiKey: BXOLZNYJTHTBKO-IZZNHLLZSA-N

物化性质

• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-deoxy-5'-O-triphenylmethylthymidine 在 溶剂黄146 作用下， 反应 0.17h， 以93%的产率得到2',3'-二脱氧胸苷
  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
• 作为产物：
  描述：

  3'-O-[(propylthio)thiocarbonyl]-5'-O-triphenylmethylthymidine 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以68%的产率得到3'-deoxy-5'-O-triphenylmethylthymidine
  参考文献：
  名称：

  保护基团转移：通过醚交换作用去除Tr和Tbdms基团的不寻常方法

  摘要：

  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。

  DOI：

  10.1080/15257770802257846

文献信息

• Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogs
  作者：Chong Ho Kim、Victor E. Marquez、Samuel Broder、Hiroaki Mitsuya、John S. Driscoll

  DOI：10.1021/jm00388a020

  日期：1987.5

  5-Substituted 2',3'-dideoxycytidine analogues have been synthesized and evaluated in vitro for their capabilities to protect T4+ lymphocytes from the cytopathic effects of the HTLV-III/LAV (HIV) virus, the causative agent of acquired immunodeficiency syndrome (AIDS). These analogues were designed to be more lipophilic than 2',3'-dideoxycytidine (ddC) in order to enhance central nervous system penetration. Earlier reports had shown that ddC is a potent protective agent. When ddC is substituted at the 5-position with either methyl or bromo substituents, activity is completely abolished. However, when the substitution is fluoro (5-F-ddC), both activity and potency are retained. 2',3'-Dideoxy-5-azacytidine is also protective but more toxic than ddC or 5-F-ddC. In a different approach, an attempt was made to utilize ddCMP, ddTMP, and ddAMP as preformed nucleotides in order to circumvent the generally low level of phosphorylation achieved with dideoxynucleosides which function as relatively poor substrates for the cellular kinases. Only ddAMP is as active as its nucleoside precursor. Because ddAMP is not more active than ddA at low concentrations, it is possible that the active agent is ddA which is generated from ddAMP prior to cell entry.
• DRISCOLL, JOHN S.;MARQUEZ, VICTOR E.;KIM, CHONG-HO;KELLEY, JAMES A.
  作者：DRISCOLL, JOHN S.、MARQUEZ, VICTOR E.、KIM, CHONG-HO、KELLEY, JAMES A.

  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
• 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。