1-(4'-benzyl-2',3'-dideoxy-α-D-ribopentofuranosyl)thymine | 1024613-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(4'-benzyl-2',3'-dideoxy-α-D-ribopentofuranosyl)thymine
• 英文别名: 1-[(2S,5R)-5-benzyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1024613-20-4
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: YMMXRVGEKLBJCH-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(2RS,5S)-5-benzyl-5-(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以46%的产率得到1-[(2S,5S)-5-benzyl-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one

  摘要：

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.028

文献信息

• Asymmetric synthesis of 4′-C-benzyl-2′,3′-dideoxynucleoside analogues from 3-benzyl-2-hydroxy-2-cyclopenten-1-one
  作者：Artur Jõgi、Marit Ilves、Anne Paju、Tõnis Pehk、Tiiu Kailas、Aleksander-Mati Müürisepp、Margus Lopp

  DOI：10.1016/j.tetasy.2008.01.028

  日期：2008.3

  Both enantiomers of the key intermediate, 2-benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid were obtained by asymmetric oxidation of 3 -benzyl-2-hyd roxy-2-cyclopen ten- 1 -one with all ee >= 96%, using the tartaric ester/Ti(OiPr)(4)/t-BuOOH complex, and transformed to the corresponding 4'-substituted nucleoside analogues with up to 61% overall yield. (C) 2008 Elsevier Ltd. All rights reserved.