3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-α-D-allopyranose | 1287194-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-α-D-allopyranose
• 英文别名: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-N-[(2S,3R,4R,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl]oxane-2-sulfonamide
• CAS: 1287194-70-0
• 化学式: C₁₂H₂₃NO₁₂S
• 分子量: 405.38
• InChiKey: SLNGEAHVDXVFPQ-KVYGWDEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  235
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-硫代-beta-D-葡萄糖五乙酸酯 在 水 、 sodium methylate 、 溴代丙二酸二乙酯 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-β-D-allopyranose 、 3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-α-D-allopyranose
  参考文献：
  名称：

  Synthesis of Sulfonamide-Bridged Glycomimetics

  摘要：

  A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1 <-> 1) and head-to-tail (1 -> 2), (1 -> 3), (1 -> 4), and (1 -> 6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.

  DOI：

  10.1021/jo2001269

文献信息

• Synthesis of Sulfonamide-Bridged Glycomimetics
  作者：Marie Lopez、Laurent F. Bornaghi、Hugues Driguez、Sally-Ann Poulsen

  DOI：10.1021/jo2001269

  日期：2011.5.6

  A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1 <-> 1) and head-to-tail (1 -> 2), (1 -> 3), (1 -> 4), and (1 -> 6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.