(2R,3R,4R,5R)-4-氟-2-(羟基甲基)-5-(2-碘-6-甲氧基嘌呤-9-基)四氢呋喃-3-醇 | 150863-85-7

• 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)-4-氟-2-(羟基甲基)-5-(2-碘-6-甲氧基嘌呤-9-基)四氢呋喃-3-醇
• 英文名称: 2-iodo-6-methoxy-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)purine
• 英文别名: 9-(2-Deoxy-2-fluororibofuranosyl)-2-iodo-6-methoxypurine；(2R,3R,4R,5R)-4-fluoro-2-(hydroxymethyl)-5-(2-iodo-6-methoxypurin-9-yl)oxolan-3-ol
• CAS: 150863-85-7
• 化学式: C₁₁H₁₂FIN₄O₄
• 分子量: 410.144
• InChiKey: RZNPNDVANHIBAN-QYYRPYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-4-氟-2-(羟基甲基)-5-(2-碘-6-甲氧基嘌呤-9-基)四氢呋喃-3-醇 在 potassium fluoride 、 氨 作用下， 以 甲醇 、 六甲基磷酰三胺 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 2'-Deoxy-2,2'-difluoro-adenosine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines

  摘要：

  2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.

  DOI：

  10.1080/15257779408012146
• 作为产物：
  描述：

  2-iodo-6-methoxy-9-(2-O-acetyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)purine 在 四丁基氟化铵 、 氨 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 溶剂黄146 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.17h， 生成 (2R,3R,4R,5R)-4-氟-2-(羟基甲基)-5-(2-碘-6-甲氧基嘌呤-9-基)四氢呋喃-3-醇
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines

  摘要：

  2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.

  DOI：

  10.1080/15257779408012146

文献信息

• Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines
  作者：Tokumi Maruyama、Kunihiko Utsumi、Yoshiko Sato、Douglas D. Richman

  DOI：10.1080/15257779408012146

  日期：1994.7

  2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.