3-deoxy-3-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose | 1287194-66-4

• 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: 3-deoxy-3-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(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]amino]sulfanyl-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 1287194-66-4
• 化学式: C₂₆H₃₉NO₁₄S
• 分子量: 621.66
• InChiKey: BROJFDZYDWEGTC-DWARJDMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-deoxy-3-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 在 sodium methylate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 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
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside 、 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 1.5h， 以73%的产率得到3-deoxy-3-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-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