[(2R,3S,5R)-3-acetyloxy-5-[5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate | 1187734-41-3

• 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: [(2R,3S,5R)-3-acetyloxy-5-[5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 1187734-41-3
• 化学式: C₂₆H₃₁N₅O₇
• 分子量: 525.561
• InChiKey: CYGSSZDYGURPCS-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  C5-Modified nucleosides exhibiting anticancer activity

  摘要：

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.072
• 作为产物：
  描述：

  4-叔丁基苄基叠氮 、 5-ethynyl-2'-deoxyuridine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 正丁醇 为溶剂， 反应 10.0h， 生成 [(2R,3S,5R)-3-acetyloxy-5-[5-[1-[(4-tert-butylphenyl)methyl]triazol-4-yl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  C5-Modified nucleosides exhibiting anticancer activity

  摘要：

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.072