3'-O-benzoyl-5'-O-p-toluenesulfonyl-thymidine | 107180-53-0

• 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: 3'-O-benzoyl-5'-O-p-toluenesulfonyl-thymidine
• 英文别名: O^3'-benzoyl-O^5'-(toluene-4-sulfonyl)-thymidine；3'-O-Benzoyl-5'-O-tosyl-thymidin；Bz(-3)[Tos(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[(4-methylphenyl)sulfonyloxymethyl]oxolan-3-yl] benzoate
• CAS: 107180-53-0
• 化学式: C₂₄H₂₄N₂O₈S
• 分子量: 500.529
• InChiKey: PKYRXBJKKTWDQE-PWRODBHTSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-5'-O-p-toluenesulfonyl-thymidine 在 四氮唑 、 叔丁基过氧化氢 、 lithium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 thymidine 5;-monolithium carboxymethylphosphate
  参考文献：
  名称：

  Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)

  摘要：

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00074-9

文献信息

• Syntheses of inhibitors for the enzyme thymidine 5′-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46)
  作者：Andreas Naundorf、Werner Klaffke

  DOI：10.1016/s0008-6215(99)00074-9

  日期：1999.5

  Inhibitors of the enzyme thymidine 5'-diphosphate-glucose-4,6-dehydratase (EC 4.2.1.46) were synthesised starting from thymidine, 2-deoxy-uridine and -cytidine. The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself. Spacers were attached to various positions, of which those at C-5 of the nucleobase were suitable analogues and showed a mixed type of inhibition characteristics, whereas attachment at other sites led to marginally active or inactive inhibitors. These investigations will prepare the ground for developing a purification procedure based on affinity chromatography. (C) 1999 Elsevier Science Ltd. All rights reserved.