1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}-5-methylpyrimidine-2,4-(1H,3H)-dione | 877621-60-8

• 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-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}-5-methylpyrimidine-2,4-(1H,3H)-dione
• 英文别名: 1-[[(3R,5S)-2-[(3aS,4S,6R,6aS)-6-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-yl]-3-(hydroxymethyl)-1,2-oxazolidin-5-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 877621-60-8
• 化学式: C₂₈H₄₁N₃O₉
• 分子量: 563.648
• InChiKey: RWAQPSRCZYHXKH-WTYJVQNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}-5-methylpyrimidine-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70.2%的产率得到{(1S,4R)-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
• 作为产物：
  描述：

  2,3:5,6-di-O-cyclohexylidene-D-mannose oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 1-{[(3R,5S)-2-(2,3:5,6-di-O-cyclohexylidene-α-D-mannofuranosyl)-3-(hydroxymethyl)-1,2-isoxazolidin-5-yl]methyl}-5-methylpyrimidine-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

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.