(2R,3R,4R,5R)-5-(6-氯嘌呤-9-基)-4-氟-2-(羟基甲基)四氢呋喃-3-醇 | 150863-84-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: (2R,3R,4R,5R)-5-(6-氯嘌呤-9-基)-4-氟-2-(羟基甲基)四氢呋喃-3-醇
• 英文名称: 6-chloro-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)purine
• 英文别名: 2’-fluoro-6-chloropurine-2’-deoxyribose；6-Chloro-9-(2-deoxy-2-fluororibofuranosyl)purine；(2R,3R,4R,5R)-5-(6-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
• CAS: 150863-84-6
• 化学式: C₁₀H₁₀ClFN₄O₃
• 分子量: 288.666
• InChiKey: HLXISARTQIJHHE-QYYRPYCUSA-N

物化性质

• 沸点：
  570.0±60.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-(6-氯嘌呤-9-基)-4-氟-2-(羟基甲基)四氢呋喃-3-醇 在 硫化氢 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到2’-fluoro-6-mercaptopurine-2’-deoxyribose
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 6-Substituted Purine 2′-Deoxy-2′-fluororibosides

  摘要：

  3',5'-Di-O-protected 6-chloropurine arabinoside 4b was treated with diethylaminosulfur trifluoride (DAST) and subsequently deprotected with pyridinium p-toluenesulfonate to give 6-chloropurine 2'-deoxy-2'-fluororiboside 6a. The displacement with nucleophile afforded the 6-substituted congener 6b-e. Treatment of 5'-O-protected 6-chloropurine arabinoside 3c with DAST gave lyxo-epoxide 7.

  DOI：

  10.1080/15257779408013260
• 作为产物：
  描述：

  6-chloro-9-(2-deoxy-2-fluoro-3,5-di-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl)purine 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以68%的产率得到(2R,3R,4R,5R)-5-(6-氯嘌呤-9-基)-4-氟-2-(羟基甲基)四氢呋喃-3-醇
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 6-Substituted Purine 2′-Deoxy-2′-fluororibosides

  摘要：

  3',5'-Di-O-protected 6-chloropurine arabinoside 4b was treated with diethylaminosulfur trifluoride (DAST) and subsequently deprotected with pyridinium p-toluenesulfonate to give 6-chloropurine 2'-deoxy-2'-fluororiboside 6a. The displacement with nucleophile afforded the 6-substituted congener 6b-e. Treatment of 5'-O-protected 6-chloropurine arabinoside 3c with DAST gave lyxo-epoxide 7.

  DOI：

  10.1080/15257779408013260

文献信息

• [EN] MODIFIED OLIGONUCLEOTIDES<br/>[FR] OLIGONUCLÉOTIDES MODIFIÉS
  申请人：[en]ALNYLAM PHARMACEUTICALS, INC.

  公开号：WO2022155418A1

  公开（公告）日：2022-07-21

  One aspect of the present invention relates to double-stranded RNA (dsRNA) molecules comprising a 6-methyladenine nucleobase and capable of inhibiting the expression of a target gene. Other aspects of the invention relate to pharmaceutical compositions comprising these dsRNA molecules suitable for therapeutic use, and methods of inhibiting the expression of a target gene by administering these dsRNA molecules, e.g., for the treatment of various disease conditions.