2-[4-[(2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]phenyl]isoindole-1,3-dione | 1293912-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[4-[(2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]phenyl]isoindole-1,3-dione
• CAS: 1293912-47-6
• 化学式: C₂₇H₂₃NO₇S
• 分子量: 505.548
• InChiKey: FKYBJQLLEOQKNJ-FZZOYGMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[4-[(2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]phenyl]isoindole-1,3-dione 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-[4-[(2R,4aR,6S,7R,8R,8aR)-7-hydroxy-6-phenylsulfanyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]phenyl]isoindole-1,3-dione
  参考文献：
  名称：

  Preparation of tagged glucose as a key intermediate in the synthesis of branched oligosaccharides

  摘要：

  Tagged and activated D-glucose was introduced as a building block for branched oligosaccharides. This building block was the oligosaccharide branching point at which selectively the C-2 followed by the C-3 position can be glycosylated. After the activation of the C-1 position by oxidation of a thiophenyl group, the newly formed tagged oligosaccharide can be used as a glycoside donor. Synthetic procedures for the preparation of phthalimide-based tag molecules as well as tagged monosaccharides are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.149
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 对甲苯磺酸一水合物 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.0h， 生成 2-[4-[(2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-2-yl]phenyl]isoindole-1,3-dione
  参考文献：
  名称：

  Preparation of tagged glucose as a key intermediate in the synthesis of branched oligosaccharides

  摘要：

  Tagged and activated D-glucose was introduced as a building block for branched oligosaccharides. This building block was the oligosaccharide branching point at which selectively the C-2 followed by the C-3 position can be glycosylated. After the activation of the C-1 position by oxidation of a thiophenyl group, the newly formed tagged oligosaccharide can be used as a glycoside donor. Synthetic procedures for the preparation of phthalimide-based tag molecules as well as tagged monosaccharides are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.149

文献信息

• Preparation of tagged glucose as a key intermediate in the synthesis of branched oligosaccharides
  作者：Sunil K. Upadhyay、Branko S. Jursic

  DOI：10.1016/j.tetlet.2011.01.149

  日期：2011.4

  Tagged and activated D-glucose was introduced as a building block for branched oligosaccharides. This building block was the oligosaccharide branching point at which selectively the C-2 followed by the C-3 position can be glycosylated. After the activation of the C-1 position by oxidation of a thiophenyl group, the newly formed tagged oligosaccharide can be used as a glycoside donor. Synthetic procedures for the preparation of phthalimide-based tag molecules as well as tagged monosaccharides are presented. (C) 2011 Elsevier Ltd. All rights reserved.