3'-O-<6-(benzyloxycarbonylamino)hexanoyl>thymidine | 168786-83-2

• 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-<6-(benzyloxycarbonylamino)hexanoyl>thymidine
• 英文别名: [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 6-(phenylmethoxycarbonylamino)hexanoate
• CAS: 168786-83-2
• 化学式: C₂₄H₃₁N₃O₈
• 分子量: 489.525
• InChiKey: PUSWXIMSMBTVSC-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-<6-(benzyloxycarbonylamino)hexanoyl>thymidine 在 sodium pyrophosphate 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 吡啶 为溶剂， 反应 120.0h， 以53%的产率得到3'-O-(6''-N-benzyloxycarbonylamino)-hexanoyl-thymidine 5'-trilithiumdiphosphate
  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 The diphosphate moieties have either been replaced by methylene diphosphonate or phosphoryl hydroxyacetic acid to yield inhibitors in a similar range to thymidine 5'-diphosphate itself.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：

  3'-O-<6-(benzyloxycarbonylamino)hexanoyl>-5'-O-dimethoxytritylthymidine 在 苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以80%的产率得到3'-O-<6-(benzyloxycarbonylamino)hexanoyl>thymidine
  参考文献：
  名称：

  Sarfati, Robert S.; Berthod, Thomas; Guerreiro, Catherine, Journal of the Chemical Society. Perkin transactions I, 1995, # 9, p. 1163 - 1172

  摘要：

  DOI：

文献信息

• Sarfati, Robert S.; Berthod, Thomas; Guerreiro, Catherine, Journal of the Chemical Society. Perkin transactions I, 1995, # 9, p. 1163 - 1172
  作者：Sarfati, Robert S.、Berthod, Thomas、Guerreiro, Catherine、Canard, Bruno

  DOI：——

  日期：——
• 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.