9-<2',3'-Dideoxy-3'-C-(hydroxymethyl)-D-erythro-pentofuranosyl>adenine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-<2',3'-Dideoxy-3'-C-(hydroxymethyl)-D-erythro-pentofuranosyl>adenine
• 英文别名: [(2S,3R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-yl]methanol；[(2S,3R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]methanol
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: ROKFTZONUGKALY-GCJDJSOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 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：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-N-(6-Chloropurin-9-yl) 5-O-benzoyl-3-C-<(benzoyloxy)methyl>-2,3-dideoxy-erythro-furanoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 9-<2',3'-Dideoxy-3'-C-(hydroxymethyl)-D-erythro-pentofuranosyl>adenine
  参考文献：
  名称：

  A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs

  摘要：

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.

  DOI：

  10.1021/jo00087a029