Methanesulfonic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl ester | 180403-68-3

• 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: Methanesulfonic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl ester
• CAS: 180403-68-3
• 化学式: C₁₂H₁₇N₅O₆S
• 分子量: 359.363
• InChiKey: YGRZNDGSBWJSFS-GRIPGOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.75
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  162.68
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylmethyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到9-[3-C-(azidomethyl)-3-deoxy-β-D-ribofuranosyl]adenine
  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)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 硫酸 、 氨 、 四氯化锡 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 177.0h， 生成 Methanesulfonic acid (2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-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