1-{(3R,5S)-2-benzyl-3-[(1S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine | 287195-06-6

• 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-{(3R,5S)-2-benzyl-3-[(1S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine
• 英文别名: 1-[(3R,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
• CAS: 287195-06-6
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: NYHZGGGEYJKBBB-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-{(3R,5S)-2-benzyl-3-[(1S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1-[(3R,5S)-2-Benzyl-3-((S)-1,2-dihydroxy-ethyl)-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Stereoselective synthesis of l -isoxazolidinyl thymidine from N -benzyl-1,2-di- O -isopropylidene- d -glyceraldehyde nitrone (BIGN)

  摘要：

  A synthetic approach to L-isoxazolidinyl nucleosides is demonstrated by the stereoselective conversion of N-benzyl-1,2-di-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) into cis and trans L-isoxazolidinyl thymidine. The methodology consists of the 1,3-dipolar cycloaddition of BIGN with either vinyl acetate or a vinyl base to give key intermediates that are easily transformed into the target compound. The experimental results of the cycloaddition reactions can be qualitatively explained by theoretical ab initio calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00094-x
• 作为产物：
  描述：

  N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 、 1-vinylthymine 以 甲苯 为溶剂， 反应 15.0h， 以64%的产率得到1-{(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine
  参考文献：
  名称：

  Stereoselective synthesis of l -isoxazolidinyl thymidine from N -benzyl-1,2-di- O -isopropylidene- d -glyceraldehyde nitrone (BIGN)

  摘要：

  A synthetic approach to L-isoxazolidinyl nucleosides is demonstrated by the stereoselective conversion of N-benzyl-1,2-di-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) into cis and trans L-isoxazolidinyl thymidine. The methodology consists of the 1,3-dipolar cycloaddition of BIGN with either vinyl acetate or a vinyl base to give key intermediates that are easily transformed into the target compound. The experimental results of the cycloaddition reactions can be qualitatively explained by theoretical ab initio calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00094-x

文献信息

• Stereoselective synthesis of l -isoxazolidinyl thymidine from N -benzyl-1,2-di- O -isopropylidene- d -glyceraldehyde nitrone (BIGN)
  作者：Pedro Merino、Eva M del Alamo、Santiago Franco、Francisco L Merchan、Ana Simon、Tomas Tejero

  DOI：10.1016/s0957-4166(00)00094-x

  日期：2000.4

  A synthetic approach to L-isoxazolidinyl nucleosides is demonstrated by the stereoselective conversion of N-benzyl-1,2-di-O-isopropylidene-D-glyceraldehyde nitrone (BIGN) into cis and trans L-isoxazolidinyl thymidine. The methodology consists of the 1,3-dipolar cycloaddition of BIGN with either vinyl acetate or a vinyl base to give key intermediates that are easily transformed into the target compound. The experimental results of the cycloaddition reactions can be qualitatively explained by theoretical ab initio calculations. (C) 2000 Elsevier Science Ltd. All rights reserved.