1-((3aR,4S,6R,6aR)-4-Azidomethyl-2-oxo-hexahydro-furo[3,4-b]furan-6-yl)-5-methyl-1H-pyrimidine-2,4-dione | 279248-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1-((3aR,4S,6R,6aR)-4-Azidomethyl-2-oxo-hexahydro-furo[3,4-b]furan-6-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(3aR,4S,6R,6aR)-4-(azidomethyl)-2-oxo-3a,4,6,6a-tetrahydro-3H-furo[2,3-c]furan-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 279248-93-0
• 化学式: C₁₂H₁₃N₅O₅
• 分子量: 307.266
• InChiKey: WCLJMUDAMBTWRS-LUQPRHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 1-((3aR,4S,6R,6aR)-4-Azidomethyl-2-oxo-hexahydro-furo[3,4-b]furan-6-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以21%的产率得到5'-azido-2'-O-(tert-butyldimethylsilyl)-3'-(carboxymethyl)-3',5'-dideoxy-5-methyluridine
  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：

  1,2-di-O-acetyl-5-azido-3,5-dideoxy-3-[(ethoxycarbonyl)methyl]-D-ribofuranose 在 硫酸氢铵 、 sodium hydroxide 、 六甲基二硅氮烷 作用下， 以 甲醇 、 水 为溶剂， 反应 120.0h， 生成 1-((3aR,4S,6R,6aR)-4-Azidomethyl-2-oxo-hexahydro-furo[3,4-b]furan-6-yl)-5-methyl-1H-pyrimidine-2,4-dione
  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

文献信息

• Glucose-Derived 3‘-(Carboxymethyl)-3‘-deoxyribonucleosides and 2‘,3‘-Lactones as Synthetic Precursors for Amide-Linked Oligonucleotide Analogues¹
  作者：Morris J. Robins、Bogdan Doboszewski、Victor A. Timoshchuk、Matt A. Peterson

  DOI：10.1021/jo991399g

  日期：2000.5.1

  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.