methyl 5-deoxy-2,3-O-isopropylidene-5-(5-methyluracil-2-yl)thio-β-D-ribofuranoside | 676557-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 5-deoxy-2,3-O-isopropylidene-5-(5-methyluracil-2-yl)thio-β-D-ribofuranoside
• 英文别名: 2-[[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylsulfanyl]-5-methyl-1H-pyrimidin-6-one
• CAS: 676557-68-9
• 化学式: C₁₄H₂₀N₂O₅S
• 分子量: 328.389
• InChiKey: MGYMMXXCWBTLMQ-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.67
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-2,3-O-isopropylidene-5-(5-methyluracil-2-yl)thio-β-D-ribofuranoside 在 溶剂黄146 作用下， 反应 2.0h， 以75%的产率得到methyl 5-deoxy-5-(5-methyluracil-2-yl)thio-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Anti-HBV Activity of Thiouracils Linked via S and N-1 to the 5-Position of Methyl β-D-Ribofuranoside

  摘要：

  Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-beta-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.

  DOI：

  10.1081/ncn-120026404
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 吡啶 、 sodium hydroxide 、 sodium iodide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 methyl 5-deoxy-2,3-O-isopropylidene-5-(5-methyluracil-2-yl)thio-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Anti-HBV Activity of Thiouracils Linked via S and N-1 to the 5-Position of Methyl β-D-Ribofuranoside

  摘要：

  Reverse nucleoside derivatives of 2-(methylsulfanyl)uracils 6a-d were prepared by treating of the sodium salt of 2-(methylsulfanyl)uracils (5a-d) with methyl 2,3-O-isopropylidene-5-O-p-toluenesulfonyl-beta-D-ribofuranoside (2). The alkylation of 2-thiouracils 4a-d with methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribofuranoside (3) afforded the corresponding S-ribofuranoside derivatives 8a-d. Deisopropylidenation of 6a-d and 8a-d afforded the corresponding deprotected derivatives 7a-d and 9a-d, respectively. The Anti-HBV activity of selected compounds was studied.

  DOI：

  10.1081/ncn-120026404