Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester | 180403-72-9

• 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: Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS: 180403-72-9
• 化学式: C₂₅H₂₂N₈O₅
• 分子量: 514.5
• InChiKey: KMQSNXOFYNCRLC-YLHGCELOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  177.22
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 叠氮化锂 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 [(2S,5R)-5-(6-aminopurin-9-yl)-3-(azidomethyl)-2,5-dihydrofuran-2-yl]methanol
  参考文献：
  名称：

  Synthesis and antiviral activity of 3′-C-branched-3′-deoxy analogues of adenosine

  摘要：

  The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described, Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-beta-D-ribofuranose (6), was prepared in three steps, Condensation of the latter with bis(trimethysilylated) N-6-benzoyladenine in the presence of tin(IV) chloride gave the N-9-beta-nucleoside 7. Compound 7 was converted into (i) 9-[3-C-(azidomethyl)-3-deoxy-beta-D-ribofuranosyl]adenine (10), (ii) 9-[3-C-(azidomethyl)-2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl]adenine (14) and 9-[2-azido-3-C-(azidomethyl)-2,3-dideoxy-beta-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-beta-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00028-6
• 作为产物：
  描述：

  {(3aR,5S,6R,6aR)-5-[(R)-1,2-Dihydroxyethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}methyl methanesulfonate 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 sodium azide 、 硫酸 、 四氯化锡 、 碳酸氢钠 、 一水合肼 、 溶剂黄146 作用下， 以 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 215.0h， 生成 Benzoic acid (2S,3S,4R,5R)-3-azidomethyl-5-(6-benzoylamino-purin-9-yl)-4-hydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis and antiviral activity of 3′-C-branched-3′-deoxy analogues of adenosine

  摘要：

  The synthesis of some 3'-C-branched-3'-deoxy adenine nucleosides is described, Starting from the known 3-deoxy-3-C-(hydroxymethyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (1), a versatile glycosylating agent, namely 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-(mesyloxymethyl)-beta-D-ribofuranose (6), was prepared in three steps, Condensation of the latter with bis(trimethysilylated) N-6-benzoyladenine in the presence of tin(IV) chloride gave the N-9-beta-nucleoside 7. Compound 7 was converted into (i) 9-[3-C-(azidomethyl)-3-deoxy-beta-D-ribofuranosyl]adenine (10), (ii) 9-[3-C-(azidomethyl)-2,3-dideoxy-beta-D-glycero-pent-2-enofuranosyl]adenine (14) and 9-[2-azido-3-C-(azidomethyl)-2,3-dideoxy-beta-D-arabinofuranosyl]adenine (15), and (iii) 9-[3-deoxy-2-O,3-C-(methylene)-beta-D-ribofuranosyl]adenine (16). None of the tested nucleosides showed marked cytostatic or antiviral activity in vitro. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0008-6215(96)00028-6