3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 1287194-68-6

• 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)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: (2S,3R,4S,5S,6R)-N-[(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-sulfonamide
• CAS: 1287194-68-6
• 化学式: C₁₈H₃₁NO₁₂S
• 分子量: 485.51
• InChiKey: NAJUHLVRMJBFPM-QELKQAQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  191
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 水 作用下， 以63%的产率得到3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-1,2-O-isopropylidene-α-D-allofuranose
  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
• 作为产物：
  描述：

  1-硫代-beta-D-葡萄糖五乙酸酯 在 sodium methylate 、 溴代丙二酸二乙酯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-deoxy-3-((β-D-glucopyranosyl)sulfonylamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
  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.