2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranosyl chloride | 61112-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranosyl chloride
• 英文别名: deca-O-acetyl-α-maltotriosyl chloride
• CAS: 61112-66-1
• 化学式: C₃₈H₅₁ClO₂₅
• 分子量: 943.261
• InChiKey: QXOWVLSKPRSDEQ-IXEGKZDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  309.15
• 氢给体数：
  0.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranosyl chloride 在 叠氮基三甲基硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 以80%的产率得到(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates

  摘要：

  Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of alpha- or beta-glycopyranosyl amides. The alpha/beta ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively alpha-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems.

  DOI：

  10.1021/ja028694u
• 作为产物：
  描述：

  β-D-maltotriose undecaacetate 在 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2,3,6-tri-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates

  摘要：

  Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of alpha- or beta-glycopyranosyl amides. The alpha/beta ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively alpha-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems.

  DOI：

  10.1021/ja028694u