2,3,4-tri-O-acetyl-6-O-allyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-allyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 761427-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-6-O-allyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-allyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS: 761427-64-9
• 化学式: C₄₀H₅₈O₂₁
• 分子量: 874.888
• InChiKey: RYDIWXNENCFLSA-XDRSXGSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  61.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  233.03
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranose 、 2,3,4-tri-O-acetyl-6-O-allyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-allyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到
  参考文献：
  名称：

  Synthesis of lactoside glycodendrons using photoaddition and reductive amination methodologies

  摘要：

  Carbohydrate-based divalent and tetravalent lactoside glycodendrons were constructed in a convergent manner. The dendrons were synthesized beginning with the photoaddition of hepta-O-acetyl-1-thio-beta-lactose, in an anti-Markovnikov manner, to a bis-allyl AB(2) trisaccharide to form a divalent dendron. Following two nearly quantitative deprotection steps, the divalent lactoside was coupled to another AB(2) trisaccharide by reductive amination to afford a tetravalent dendron. These paucivalent compounds were characterized by NMR spectroscopy and mass spectrometry. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.011
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-α-D-glucopyranosyl-(1-4)-2,3-di-O-acetyl-4-tert-butyldimethylsilyl-β-D-glucopyranosyl-(1-6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 三氟甲磺酸 、 一溴化碘 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 23.0h， 生成 2,3,4-tri-O-acetyl-6-O-allyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-allyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of lactoside glycodendrons using photoaddition and reductive amination methodologies

  摘要：

  Carbohydrate-based divalent and tetravalent lactoside glycodendrons were constructed in a convergent manner. The dendrons were synthesized beginning with the photoaddition of hepta-O-acetyl-1-thio-beta-lactose, in an anti-Markovnikov manner, to a bis-allyl AB(2) trisaccharide to form a divalent dendron. Following two nearly quantitative deprotection steps, the divalent lactoside was coupled to another AB(2) trisaccharide by reductive amination to afford a tetravalent dendron. These paucivalent compounds were characterized by NMR spectroscopy and mass spectrometry. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.06.011