3-benzyl-1-((3aR,4R,6R,6aR)-6-((((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione | 1160622-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyl-1-((3aR,4R,6R,6aR)-6-((((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1160622-70-7
• 化学式: C₄₆H₅₀N₂O₁₀
• 分子量: 790.91
• InChiKey: VAVWQARWQSRELB-DZTYRHCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  58.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  117.84
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-((3aR,4R,6R,6aR)-6-((((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione 在 Pd(OH)2/C 、 环己烯 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N(3)-benzyl-2',3'-O-isopropylidene-5'-(2-deoxy-β-D-glucopyranosyl)uridine
  参考文献：
  名称：

  Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

  摘要：

  Synthesis of N3,2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy--d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.

  DOI：

  10.1080/15257770802458303
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 N³-benzyl-2',3'-O-isopropylideneuridine 在 四苯基硼酸钠盐 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-benzyl-1-((3aR,4R,6R,6aR)-6-((((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

  摘要：

  Synthesis of N3,2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy--d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.

  DOI：

  10.1080/15257770802458303