2-amino-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine | 847654-59-5

• 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: 2-amino-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine
• CAS: 847654-59-5
• 化学式: C₃₁H₃₁N₅O₄
• 分子量: 537.618
• InChiKey: RLPCSQQNTKLINK-PJCXANEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  106.54
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-amino-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以58.6%的产率得到9-β-D-arabinofuranosyl-2-aminopurine
  参考文献：
  名称：

  Stereoselective synthesis of 9-β-d-arabianofuranosyl guanine and 2-amino-9-(β-d-arabianofuranosyl)purine

  摘要：

  9- beta- D -Arabian ofuranosyl guanine (6) and 2-amino-9-(beta-D-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-p-D-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-D-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only P-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1: 1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.029
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 4 A molecular sieve 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 151.0h， 生成 2-amino-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine
  参考文献：
  名称：

  Stereoselective synthesis of 9-β-d-arabianofuranosyl guanine and 2-amino-9-(β-d-arabianofuranosyl)purine

  摘要：

  9- beta- D -Arabian ofuranosyl guanine (6) and 2-amino-9-(beta-D-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-p-D-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-D-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only P-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1: 1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.029