5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine | 246022-21-9

• 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-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine
• 英文别名: Thymidine, 5a(2)-O-[bis(4-methoxyphenyl)phenylmethyl]-4a(2)-C-ethenyl-；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-ethenyl-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 246022-21-9
• 化学式: C₃₃H₃₄N₂O₇
• 分子量: 570.642
• InChiKey: ICMZYOBXZPYAKA-NPLMNSEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4'-vinylthymidine
  参考文献：
  名称：

  核苷和核苷酸。183.4'α-支链胸苷的合成作为新型抗病毒剂。

  摘要：

  合成了一系列的4'α-支化胸腺嘧啶核苷，并将其评估为潜在的抗病毒药。4'-乙基胸苷（3），4'-乙烯基胸苷（5）和4'-乙炔基胸腺嘧啶（6）表现出有效的抗HSV-1和抗HIV-1活性，且无明显细胞毒性。

  DOI：

  10.1016/s0960-894x(99)00010-4
• 作为产物：
  描述：

  1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-5-phenylselanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 4-二甲氨基吡啶 、 六正丁基二锡 、 三乙胺 作用下， 以 甲苯 、 苯 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-4'αC-vinylthymidine
  参考文献：
  名称：

  A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-C-Vinylthymidine, a Potent Antiviral Nucleoside¹

  摘要：

  A one-pot method for the stereoselective introduction of a vinyl group at the beta-position of a hydroxyl group in halohydrins or alpha-phenylselenoalkanols via an atom-transfer radical-cyclization reaction was developed. When a solution of the diphenylvinylsilyl ether of (+/-)-trans-2-iodoindanol (2a) and (Bu3Sn)(2) in benzene was irradiated with a high-pressure mercury lamp, the corresponding atom transfer 5-exo-cyclization product was produced, which in turn was treated with tetrabutylammonium fluoride to give cis-2-vinylindanol (3) in 82% yield from 2a. Similar reactions with diphenylvinylsilyl ethers of (+/-)trans-1-phenylselenoindan-2-ol (4), trans-2-iodocyclopentanol (6), and trans-2-iodocyclohexanol (8) gave the corresponding vinyl derivatives. Furthermore, this reaction was successfully applied to the synthesis of 4'alpha-C-vinylthymidine, a potent antiviral nucleoside.

  DOI：

  10.1021/jo990787f

文献信息

• A One-Pot Method for the Stereoselective Introduction of a Vinyl Group via an Atom-Transfer Radical-Cyclization Reaction with a Diphenylvinylsilyl Group as a Temporary Connecting Tether. Synthesis of 4‘α-<i>C</i>-Vinylthymidine, a Potent Antiviral Nucleoside¹
  作者：Isamu Sugimoto、Satoshi Shuto、Akira Matsuda

  DOI：10.1021/jo990787f

  日期：1999.9.1

  A one-pot method for the stereoselective introduction of a vinyl group at the beta-position of a hydroxyl group in halohydrins or alpha-phenylselenoalkanols via an atom-transfer radical-cyclization reaction was developed. When a solution of the diphenylvinylsilyl ether of (+/-)-trans-2-iodoindanol (2a) and (Bu3Sn)(2) in benzene was irradiated with a high-pressure mercury lamp, the corresponding atom transfer 5-exo-cyclization product was produced, which in turn was treated with tetrabutylammonium fluoride to give cis-2-vinylindanol (3) in 82% yield from 2a. Similar reactions with diphenylvinylsilyl ethers of (+/-)trans-1-phenylselenoindan-2-ol (4), trans-2-iodocyclopentanol (6), and trans-2-iodocyclohexanol (8) gave the corresponding vinyl derivatives. Furthermore, this reaction was successfully applied to the synthesis of 4'alpha-C-vinylthymidine, a potent antiviral nucleoside.
• Nucleosides and nucleotides. 183. Synthesis of 4′ α-branched thymidines as a new type of antiviral agent
  作者：Isamu Sugimoto、Satoshi Shuto、Shuichi Mori、Shiro Shigeta、Akira Matsuda

  DOI：10.1016/s0960-894x(99)00010-4

  日期：1999.2

  A series of 4'alpha-branched thymidines was synthesized and evaluated as potential antiviral agents. 4'-Ethylthymidine (3), 4'-ethenylthymidine (5), and 4'-ethynylthymidine (6) exhibited potent anti-HSV-1 and anti-HIV-1 activities with no significant cytotoxicity.

  合成了一系列的4'α-支化胸腺嘧啶核苷，并将其评估为潜在的抗病毒药。4'-乙基胸苷（3），4'-乙烯基胸苷（5）和4'-乙炔基胸腺嘧啶（6）表现出有效的抗HSV-1和抗HIV-1活性，且无明显细胞毒性。