3-benzoyl-5-methyl-1-[(3R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]pyrimidine-2,4-dione | 1053648-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzoyl-5-methyl-1-[(3R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]pyrimidine-2,4-dione
• CAS: 1053648-64-8
• 化学式: C₃₂H₃₂N₂O₆
• 分子量: 540.616
• InChiKey: BCWFUFBGZINBRJ-SSBOKUKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-benzoyl-5-methyl-1-[(3R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]pyrimidine-2,4-dione 在 palladium dihydroxide sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 环己烯 为溶剂， 反应 28.0h， 生成 1-((3R,5S,6R)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-d-ribohexitol Nucleosides)

  摘要：

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.

  DOI：

  10.1021/jo961982m
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (1S,2S,4R)-2-benzyloxy-1-benzyloxymethyl-5-(2,2-dimethyl-propionyloxy)-4-(tetrahydro-pyran-2-yloxy)-pentyl ester 在 sodium hydroxide 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 3-benzoyl-5-methyl-1-[(3R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-d-ribohexitol Nucleosides)

  摘要：

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.

  DOI：

  10.1021/jo961982m

文献信息

• Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-<scp>d</scp>-ribohexitol Nucleosides)
  作者：Nafizal Hossain、Jef Rozenski、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jo961982m

  日期：1997.4.1

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.