(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(pyridin-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 124925-07-1

• 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: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(pyridin-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-pyridin-2-ylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 124925-07-1
• 化学式: C₂₅H₃₂N₂O₁₂S
• 分子量: 584.601
• InChiKey: WBQBYRIHDDBOIO-XHTNTSLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(pyridin-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 samarium diiodide 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  肿瘤相关的SialylTn抗原的二糖成分的碳连接模拟物的合成。

  摘要：

  DOI：

  10.1002/anie.200351969
• 作为产物：
  描述：

  2-巯基吡啶 、 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以69%的产率得到(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(pyridin-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors

  摘要：

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.

  DOI：

  10.1016/s0957-4166(00)86308-9

文献信息

• Anomeric Acetates ofN-Acetylneuraminic Acid are UsefulC-Sialyl Donors in Samarium-Mediated Reformatsky Coupling Reactions
  作者：Adeline Malapelle、Zouleika Abdallah、Gilles Doisneau、Jean-Marie Beau

  DOI：10.1002/anie.200601209

  日期：2006.9.11
• Anomeric Samarium(III) Intermediates of N-Acetylneuraminic Acid from Anomeric 2-Pyridylsulfides
  作者：Jean-Marie Beau、Adeline Malapelle、Zouleika Abdallah、Gilles Doisneau

  DOI：10.3987/com-08-s(f)118

  日期：——

  Treatment of the anomeric 2-thiopyridyl derivative of N-acetylneuraminic acid (sialic acid or Neu5Ac) with samarium diiodide in the presence of aldehydes or ketones provides the corresponding C-sialylated derivatives in excellent yields. The efficiency of the reductive samariation of the anomeric 2-pyridyl sulfide moiety in the Neu5Ac series does not require any cosolvent or additive. This samarium Reformatsky-like reaction from anomeric 2-pyridyl sulfide derivatives of Neu5Ac provides an efficient and highly stereoselective access to alpha-2,6-C-disaccharides.