1-(5-O-trityl-2-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil | 166813-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(5-O-trityl-2-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil
• 英文别名: 1-[(2R,4R,5R)-4-hydroxy-5-(trityloxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 166813-01-0
• 化学式: C₂₈H₂₆N₂O₄S
• 分子量: 486.591
• InChiKey: CFOBDBYLDYDSIB-DGWZTRNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-O-trityl-2-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到1-((2R,4R,5R)-4-Fluoro-5-trityloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups

  摘要：

  Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were confirmed by X-ray analysis.

  DOI：

  10.1016/s0040-4039(00)78345-6
• 作为产物：
  描述：

  1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 三溴化硼 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 1-(5-O-trityl-2-deoxy-4-thio-β-D-threo-pentofuranosyl)uracil
  参考文献：
  名称：

  Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups

  摘要：

  Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were confirmed by X-ray analysis.

  DOI：

  10.1016/s0040-4039(00)78345-6

文献信息

• Unanticipated retention of configuration in the DAST fluorination of deoxy-4′-thiopyrimidine nucleosides with “up” hydroxyl groups
  作者：Lak S. Jeong、Marc C. Nicklaus、Cliff George、Victor E. Marquez

  DOI：10.1016/s0040-4039(00)78345-6

  日期：1994.10

  Fluorination of 1-(5-O-trityl-3-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (17) and 1-(5-O-trityl-2-deoxy-4-thio-beta-D-threo-pentofuranosyl)uracil (20) with DAST proceeded with exclusive retention of configuration. The structures of the products were confirmed by X-ray analysis.
• Synthesis and Biological Activity of Sugar-Fluorinated 2',3'-dideoxy-4'-thioribofuranosyl Nucleosides
  作者：Victor Marquez、Lak Jeong、Marc Nicklaus、Cliff George

  DOI：10.1080/15257779508012426

  日期：1995.5.1