N-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thio)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine | 1287194-30-2

• 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: N-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thio)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylamino]oxan-2-yl]methyl acetate
• CAS: 1287194-30-2
• 化学式: C₂₈H₃₉NO₁₈S
• 分子量: 709.68
• InChiKey: BOUMCMHNIMAABW-HYSGBLIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  266
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  N-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thio)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到N-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfonyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
  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：

  2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 、 1-硫代-beta-D-葡萄糖五乙酸酯 在 溴代丙二酸二乙酯 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以43%的产率得到N-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thio)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
  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