[2-(dimethylamino)-2-oxoethyl] (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 345209-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(dimethylamino)-2-oxoethyl] (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 345209-48-5
• 化学式: C₅₁H₆₄N₂O₁₉
• 分子量: 1009.07
• InChiKey: GDPPWNYZNWBMOM-HNDDZXOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  72
• 可旋转键数：
  29
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  246
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [2-(dimethylamino)-2-oxoethyl] (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以24%的产率得到(2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  A New C(1)-Auxiliary for Anomeric Stereocontrol in the Synthesis of α-Sialyl Glycosides

  摘要：

  [GRAPHICS]The installation of the novel N,N-dimethylglycolamide ester auxiliary onto the C(1)-position of protected neuraminic acid donors allows for the exploitation of C(1)-neighboring group participation to generate sialoside conjugates with good to excellent or-selectivity under a variety of sialylation protocols, including those that would otherwise lead to nonselective or beta -selective sialoside products.

  DOI：

  10.1021/ol015854i
• 作为产物：
  描述：

  2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure 在 disodium hydrogenphosphate 、 silver trifluoromethanesulfonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 [2-(dimethylamino)-2-oxoethyl] (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  A New C(1)-Auxiliary for Anomeric Stereocontrol in the Synthesis of α-Sialyl Glycosides

  摘要：

  [GRAPHICS]The installation of the novel N,N-dimethylglycolamide ester auxiliary onto the C(1)-position of protected neuraminic acid donors allows for the exploitation of C(1)-neighboring group participation to generate sialoside conjugates with good to excellent or-selectivity under a variety of sialylation protocols, including those that would otherwise lead to nonselective or beta -selective sialoside products.

  DOI：

  10.1021/ol015854i

文献信息

• Dehydrative Sialylation with C2-Hemiketal Sialyl Donors
  作者：Jannine M. Haberman、David Y. Gin

  DOI：10.1021/ol034815z

  日期：2003.7.1

  [GRAHPICS]A new method for sialylation involving the dehydrative coupling of sialyl donors with the reagent combination of (p-nitrophenyl)(phenyl) sulfoxide and triflic anhydride is reported. This process establishes sialyl C2-hemiketals as viable sialyl donors for complex carbohydrate synthesis.