{(1R,4S)-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-2-oxa-3-azacyclopent-4-yl}methanol | 877621-75-5

• 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: {(1R,4S)-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-2-oxa-3-azacyclopent-4-yl}methanol
• 英文别名: 1-[[(3S,5R)-3-(hydroxymethyl)-1,2-oxazolidin-5-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 877621-75-5
• 化学式: C₁₀H₁₅N₃O₄
• 分子量: 241.247
• InChiKey: OATMRYDYIXUZAO-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {(1R,4S)-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-2-oxa-3-azacyclopent-4-yl}methanol 、 (-)-(R)-α-methoxy-α-(9-anthryl)acetic acid 在 N-[(2,4-二氯苯氧基)-甲氧基硫代膦酰]丙-2-胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到{(3S,5R)-5-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidin-3-yl}methyl (2R)-(9-anthryl)(hydroxy)acetate
  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-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]isoxazolidine-3-carboxylate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 {(1R,4S)-1-[(5-methyl-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

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.