5-fluoro-1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl}methyl)pyrimidine-2,4(1H,3H)-dione | 877621-34-6

• 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: 5-fluoro-1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl}methyl)pyrimidine-2,4(1H,3H)-dione
• CAS: 877621-34-6
• 化学式: C₃₃H₄₂FN₃O₈Si
• 分子量: 655.796
• InChiKey: PLSSNFPALIADAN-XQVJXUQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124.48
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-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74%的产率得到{(1R,4S)-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 (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-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64.52%的产率得到5-fluoro-1-({(3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-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