1-(2,3-dideoxy-3-methylthio-β-D-erythro-pentofuranosyl)thymine | 127908-94-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2,3-dideoxy-3-methylthio-β-D-erythro-pentofuranosyl)thymine
• 英文别名: Thymidine, 3'-S-methyl-3'-thio-；1-[(2R,4S,5R)-5-(hydroxymethyl)-4-methylsulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 127908-94-5
• 化学式: C₁₁H₁₆N₂O₄S
• 分子量: 272.325
• InChiKey: YIGBHTQIPVBKNR-HRDYMLBCSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,3-dideoxy-3-methylthio-β-D-erythro-pentofuranosyl)thymine 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5'-O-benzoyl-3'-deoxy-3'-(methylsulfinyl)thymidine
  参考文献：
  名称：

  Herdewijn, Piet; Bruyn, Andre De; Wigerinck, Piet, Journal of the Chemical Society. Perkin transactions I, 1994, # 3, p. 249 - 256

  摘要：

  DOI：
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.5h， 生成 1-(2,3-dideoxy-3-methylthio-β-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Convergent synthesis of 2′,3′-dideoxy-3′-methylthio and 2′,3′-dideoxy-3′-mercapto nucleosides and their disulfide analogues — Potential anti-HIV agents

  摘要：

  The iodide 4(alpha) or 7 synthesized in three steps from 2-deoxy-D-ribose 1, has been subjected to a number of nucleophilic substitution reactions producing the 3-benzoylthio-, 3-methylthio- and the 3-thiocyanato-2,3-dideoxy-D-erythro-pentofuranosides 8,13 and 15, respectively, in addition to the disulfide 17 of their 3-mercapto analogue. Subjecting the thiobenzoate 8 to the Friedel-Crafts catalyzed silyl Hilbert Johnson reaction in conjunction with the silylated nucleobases of uracil, thymine and N4-isobutyrylcytosine 9a-c resulted in the isolation of the 2',3'-dideoxy-3'-mercapto nucleosides 11 and their disulfides 12 subsequent to deprotection. The 2,3-dideoxy-3-methylthio-pentofuranoside 13 afforded both anomers of the 2',3'-dideoxy-3'-methylthio nucleosides 19 and 20 under similar conditions. The first known example of a coupling directly on a 2,3-didehydro-2,3-dideoxyfuranose is presented. 2',3'-Dideoxy-3'-mercaptocytidine showed protection against HIV-1 in MT-4 cells with ED50 = 20 muM.

  DOI：

  10.1007/bf00808508

文献信息

• Convergent synthesis of 2′,3′-dideoxy-3′-methylthio and 2′,3′-dideoxy-3′-mercapto nucleosides and their disulfide analogues — Potential anti-HIV agents
  作者：Kim L. Dueholm、Youssef L. Aly、Per T. Jørgensen、Ahmed A. El-Barbary、Erik B. Pedersen、Claus Nielsen

  DOI：10.1007/bf00808508

  日期：1993.1

  The iodide 4(alpha) or 7 synthesized in three steps from 2-deoxy-D-ribose 1, has been subjected to a number of nucleophilic substitution reactions producing the 3-benzoylthio-, 3-methylthio- and the 3-thiocyanato-2,3-dideoxy-D-erythro-pentofuranosides 8,13 and 15, respectively, in addition to the disulfide 17 of their 3-mercapto analogue. Subjecting the thiobenzoate 8 to the Friedel-Crafts catalyzed silyl Hilbert Johnson reaction in conjunction with the silylated nucleobases of uracil, thymine and N4-isobutyrylcytosine 9a-c resulted in the isolation of the 2',3'-dideoxy-3'-mercapto nucleosides 11 and their disulfides 12 subsequent to deprotection. The 2,3-dideoxy-3-methylthio-pentofuranoside 13 afforded both anomers of the 2',3'-dideoxy-3'-methylthio nucleosides 19 and 20 under similar conditions. The first known example of a coupling directly on a 2,3-didehydro-2,3-dideoxyfuranose is presented. 2',3'-Dideoxy-3'-mercaptocytidine showed protection against HIV-1 in MT-4 cells with ED50 = 20 muM.
• Herdewijn, Piet; Bruyn, Andre De; Wigerinck, Piet, Journal of the Chemical Society. Perkin transactions I, 1994, # 3, p. 249 - 256
  作者：Herdewijn, Piet、Bruyn, Andre De、Wigerinck, Piet、Hendrix, Chris、Kerremans, Luk、et al.

  DOI：——

  日期：——