ethyl (3S,5S)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (3S,5S)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate
• 英文别名: ethyl (3S,5S)-2-[(3aR,4R,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-[(5-methyl-2,4-dioxopyrimidin-1-yl)methyl]-1,2-oxazolidine-3-carboxylate
• 化学式: C₃₆H₄₇N₃O₉Si
• 分子量: 693.869
• InChiKey: UGCYPKLFJVQPHU-SPFXMBEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙醇酸乙酯 、 (4S,5R)-5-[(1R)-2-[[1-(tert-butyl)-1,1-diphenylsilyl]oxy]-1-hydroxyethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime 、 1-烯丙基-5-甲基嘧啶-2,4(1H,3H)-二酮 以 甲苯 为溶剂， 反应 12.0h， 以64.7%的产率得到ethyl (3S,5R)-2-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-β-D-ribofuranosyl]-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate
  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

文献信息

• Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides
  作者：Ugo Chiacchio、Maria Grazia Saita、Lia Crispino、Giuseppe Gumina、Sergio Mangiafico、Venerando Pistarà、Giovanni Romeo、Anna Piperno、Erik De Clercq

  DOI：10.1016/j.tet.2005.10.075

  日期：2006.2

  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.