5-fluoro-1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}pyrimidine-2,4-(1H,3H)-dione | 877621-62-0

• 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: 5-fluoro-1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}pyrimidine-2,4-(1H,3H)-dione
• CAS: 877621-62-0
• 化学式: C₂₇H₃₈FN₃O₉
• 分子量: 567.612
• InChiKey: OCXPNEYAZSBHIQ-FFCFYTQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  133.71
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}pyrimidine-2,4-(1H,3H)-dione 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以52%的产率得到{(1S,4R)-1-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-2-oxa-3-azacyclopent-4-yl}methanol
  参考文献：
  名称：

  Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides

  摘要：

  The enantioselective synthesis of homocarbocyclic-2'oxo-3'-azanucleosides has been performed by cycloaddition reaction of the N-glycosyl nitrones with allyl nucleobases. The use of nitrones originated from two different carbohydrates, the N-ribosyl nitrone and the N-mannosyl nitrone, proceeded in a stereocontrolled and predictable manner with a good degree of enantioselectivity, so allowing an easy entry to both enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.075
• 作为产物：
  描述：

  ethyl (3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-5-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以43%的产率得到5-fluoro-1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}pyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides

  摘要：

  The enantioselective synthesis of homocarbocyclic-2'oxo-3'-azanucleosides has been performed by cycloaddition reaction of the N-glycosyl nitrones with allyl nucleobases. The use of nitrones originated from two different carbohydrates, the N-ribosyl nitrone and the N-mannosyl nitrone, proceeded in a stereocontrolled and predictable manner with a good degree of enantioselectivity, so allowing an easy entry to both enantiomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.075