benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside | 1287768-36-8

• 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-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside
• 英文别名: prop-2-ynyl(-3)[Bn(-6)]GalNAc4Ac(b)-O-Bn；[(2R,3R,4R,5R,6R)-5-acetamido-6-phenylmethoxy-2-(phenylmethoxymethyl)-4-prop-2-ynoxyoxan-3-yl] acetate
• CAS: 1287768-36-8
• 化学式: C₂₇H₃₁NO₇
• 分子量: 481.546
• InChiKey: MLVXHYBSEKRVSO-IURCNINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 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 22.0h， 生成 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

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.