2-Amino-9-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol | 85572-58-3

• 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-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol
• CAS: 85572-58-3
• 化学式: C₃₁H₃₁N₅O₅
• 分子量: 553.618
• InChiKey: WITHPBZRYUQHFM-JVYBIVSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41.0
• 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：
  126.77
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-Amino-9-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以67.1%的产率得到9-Β-D-糖呋喃鸟嘌呤
  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：

  2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride 在 4 A molecular sieve 、 sodium methylate 、 2-巯基乙醇 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 168.0h， 生成 2-Amino-9-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol
  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