2'-O-acetyl-5'-azido-3',5'-dideoxy-3'-[(ethoxycarbonyl)methyl]adenosine | 279248-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2'-O-acetyl-5'-azido-3',5'-dideoxy-3'-[(ethoxycarbonyl)methyl]adenosine
• 英文别名: ethyl 2-[(2S,3R,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(azidomethyl)oxolan-3-yl]acetate
• CAS: 279248-84-9
• 化学式: C₁₆H₂₀N₈O₅
• 分子量: 404.385
• InChiKey: MENOOTGTIWOIQX-OMBOPSAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-5'-azido-3',5'-dideoxy-3'-[(ethoxycarbonyl)methyl]adenosine 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 240.0h， 生成 5'-azido-2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3',5'-dideoxyadenosine
  参考文献：
  名称：

  Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹

  摘要：

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.

  DOI：

  10.1021/jo991399g
• 作为产物：
  描述：

  腺嘌呤 、 1,2-di-O-acetyl-5-azido-3,5-dideoxy-3-[(ethoxycarbonyl)methyl]-D-ribofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以96%的产率得到2'-O-acetyl-5'-azido-3',5'-dideoxy-3'-[(ethoxycarbonyl)methyl]adenosine
  参考文献：
  名称：

  Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹

  摘要：

  Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.

  DOI：

  10.1021/jo991399g