benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside | 1287768-34-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside
• 英文别名: prop-2-ynyl(-3)[Bn(-6)]GalNAc(b)-O-Bn；N-[(2R,3R,4R,5R,6R)-5-hydroxy-2-phenylmethoxy-6-(phenylmethoxymethyl)-4-prop-2-ynoxyoxan-3-yl]acetamide
• CAS: 1287768-34-6
• 化学式: C₂₅H₂₉NO₆
• 分子量: 439.508
• InChiKey: HHSHMJNUSHOPGY-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以88%的产率得到benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 barium(II) hydroxide 、 barium(II) oxide 、 scandium tris(trifluoromethanesulfonate) 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z

文献信息

• Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks
  作者：Smritilekha Bera、Robert J. Linhardt

  DOI：10.1021/jo200076z

  日期：2011.5.6

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.