N¹-(2,3-O-isopropylidene-α-D-ribofuranosyl)inosine | 175470-38-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N¹-(2,3-O-isopropylidene-α-D-ribofuranosyl)inosine
• CAS: 175470-38-9
• 化学式: C₁₈H₂₄N₄O₉
• 分子量: 440.41
• InChiKey: UZLSYAOHROCXCH-DLFWLGJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  170.55
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N¹-(2,3-O-isopropylidene-α-D-ribofuranosyl)inosine 在 溶剂黄146 作用下， 反应 12.0h， 以32%的产率得到N¹-(α-D-ribofuranosyl)inosine
  参考文献：
  名称：

  Ribosylation of the Base Residue of Inosine Derivatives by Phase-Transfer Catalysis

  摘要：

  Reaction of 2',3',5'-O -silylated inosine derivative 1 with 2,3-O-isopropylidene-5-O-tritylribosyl chloride (3) in a two-phase (CH2Cl2-aq. NaOH) system in the presence of Bu(4)NBr gave three products, i.e., 6-O-alpha-, 6-O-beta-, and N-1-beta-isomers of glycoside a 4, 5a, and 5b. A similar PTC reaction of 1 with 2,3,5-tri-O-benzylribosyl bromide (9) gave four regio- and stereo-isomers involving the N-1-beta-glycoside 10. Reaction of 1 with 2,3,5-tri-O benzoylribosyl bromide (11) afforded three products involving the desired N-1-beta-glycoside 12b, which could be deprotected to give N-1-ribosylinosine (15b) as a useful intermediate for the synthesis of cIDPR.

  DOI：

  10.1080/07328319608002366
• 作为产物：
  描述：

  N¹-(5-O-trityl-2,3-O-isopropylidene-α-D-ribofuranosyl)inosine 在 溶剂黄146 作用下， 反应 12.0h， 以63%的产率得到N¹-(2,3-O-isopropylidene-α-D-ribofuranosyl)inosine
  参考文献：
  名称：

  Ribosylation of the Base Residue of Inosine Derivatives by Phase-Transfer Catalysis

  摘要：

  Reaction of 2',3',5'-O -silylated inosine derivative 1 with 2,3-O-isopropylidene-5-O-tritylribosyl chloride (3) in a two-phase (CH2Cl2-aq. NaOH) system in the presence of Bu(4)NBr gave three products, i.e., 6-O-alpha-, 6-O-beta-, and N-1-beta-isomers of glycoside a 4, 5a, and 5b. A similar PTC reaction of 1 with 2,3,5-tri-O-benzylribosyl bromide (9) gave four regio- and stereo-isomers involving the N-1-beta-glycoside 10. Reaction of 1 with 2,3,5-tri-O benzoylribosyl bromide (11) afforded three products involving the desired N-1-beta-glycoside 12b, which could be deprotected to give N-1-ribosylinosine (15b) as a useful intermediate for the synthesis of cIDPR.

  DOI：

  10.1080/07328319608002366