1-(2'-脱氧-beta-D-吡喃葡萄糖基)胸腺嘧啶 | 5116-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-(2'-脱氧-beta-D-吡喃葡萄糖基)胸腺嘧啶
• 英文名称: 1-(2-deoxy-D-arabino-hexopyranosyl)thymine
• 英文别名: 1-(2-deoxy-β-D-arabino-hexopyranosyl)thymine；1-(2-Deoxy-1-glycosyl)thymin；1-(β-D-arabino-2-deoxy-hexopyranosyl)-5-methyl-1H-pyrimidine-2,4-dione；Deoxyglucopyranosylthymine；1-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 5116-45-0
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: VVJYUAYZJAKGRQ-BGZDPUMWSA-N

物化性质

• 熔点：
  230 °C(Solv: water (7732-18-5))
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2'-脱氧-beta-D-吡喃葡萄糖基)胸腺嘧啶 在 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 sodium azide 、 三氟乙酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 1-(3-azido-2,3-dideoxy-β-D-ribo-hexopyranosyl)thymine
  参考文献：
  名称：

  SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES

  摘要：

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.

  DOI：

  10.1081/scc-120003150
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.5h， 生成 1-(2'-脱氧-beta-D-吡喃葡萄糖基)胸腺嘧啶
  参考文献：
  名称：

  SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES

  摘要：

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.

  DOI：

  10.1081/scc-120003150

文献信息

• Antitumor agent
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0287128A1

  公开（公告）日：1988-10-19

  The present invention relates to a composition for treatment of cancer which comprises effective amounts of a halogenated cytidine, a cytidine deaminase inhibitor, and a uridine phosphorylase inhibitor.

  本发明涉及一种治疗癌症的组合物，它包含有效量的卤代胞苷、胞苷脱氨酶抑制剂和尿苷磷酸化酶抑制剂。
• Herdeweijn, P.; Aerschot, A. Van, Bulletin des Societes Chimiques Belges, 1990, vol. 99, p. 895 - 901
  作者：Herdeweijn, P.、Aerschot, A. Van

  DOI：——

  日期：——