methyl 4-deoxy-4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-α-D-glucopyranoside | 1287194-34-6

• 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: methyl 4-deoxy-4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]amino]sulfanyloxan-2-yl]methyl acetate
• CAS: 1287194-34-6
• 化学式: C₂₁H₃₃NO₁₄S
• 分子量: 555.557
• InChiKey: AVPLTNUJNBERDZ-BHOWHMKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  231
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 4-deoxy-4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-α-D-glucopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到methyl 4-deoxy-4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfonylamino)-α-D-glucopyranoside
  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：

  methyl 4-amino-4-deoxy-α-D-glucopyranoside 、 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73%的产率得到methyl 4-deoxy-4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioamino)-α-D-glucopyranoside
  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