1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone | 108441-68-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-methoxy-5-methyl-pyrimidin-2-one；1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-4-methoxy-5-methylpyrimidin-2-one
• CAS: 108441-68-5
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: INEFBFVRASRYAP-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone 在 Dowex 50 作用下， 以 乙醇 、 水 为溶剂， 生成 齐多夫定
  参考文献：
  名称：

  Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation

  摘要：

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.

  DOI：

  10.1016/s0040-4039(00)73186-8
• 作为产物：
  描述：

  [(2S,3S,5R)-3-azido-5-phenylsulfanyloxolan-2-yl]methanol 在 sodium hydroxide 、 dimethyl(methylthio)sulfonium tetrafluoroborate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-4-methoxy-5-methyl-2(1H)-pyrimidinone
  参考文献：
  名称：

  Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation

  摘要：

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.

  DOI：

  10.1016/s0040-4039(00)73186-8

文献信息

• US5811540A
  申请人：——

  公开号：US5811540A

  公开（公告）日：1998-09-22
• Stereocontrolled synthesis of pyrimidine 2′,3′-dideoxy-β-nucleosides by intramolecular glycosylation
  作者：Keiko Sujino、Hideyuki Sugimura

  DOI：10.1016/s0040-4039(00)73186-8

  日期：1994.3

  beta-2',3'-Dideoxynucleosides and their 3'-azido and 3'-fluoro substituted derivatives were synthesized in a stereocontrolled manner by th dimethyl(methylthio)sulfonium tetrafluoroborate promoted intramolecular glycosylation of phenyl 2,3-dideoxy-5-O-(2-pyrimidyl)-1-thioglycosides followed by hydrolysis or ammonolysis.