3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate | 249286-87-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate
• 英文别名: [(2R,3S,5R)-2-[[2-cyanoethoxy-(2-methoxy-2-oxoethoxy)phosphoryl]oxymethyl]-5-[2,4-dioxo-5-[8-[(2,2,2-trifluoroacetyl)amino]oct-1-ynyl]pyrimidin-1-yl]oxolan-3-yl] benzoate
• CAS: 249286-87-1
• 化学式: C₃₂H₃₆F₃N₄O₁₂P
• 分子量: 756.626
• InChiKey: BWNGREUMEIQFCI-VERBLDJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  209
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate 在 lithium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以91%的产率得到2'-deoxyuridine 5'-monolithium-methoxycarbonylmethyl phosphate
  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 The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself.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
• 作为产物：
  描述：

  2'-脱氧-5'-O-[(叔丁基)二甲基硅烷基]-5-碘尿苷 在 吡啶 、 四氮唑 、 叔丁基过氧化氢 、 copper(l) iodide 、 tris(triphenylphosphine)-palladium(II) dichloride 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 三乙胺 、 乙腈 为溶剂， 反应 12.0h， 生成 3'-O-benzoyl-2'-deoxy-5-(8-trifluoracetamidooct-1-ynyl)uridine 5'-(2-cyanoethoxy)-methoxycarbonylmethyl phosphate
  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