7-octen-1-yl 2-acetamido-3-O-(2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranoside | 1321579-60-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-octen-1-yl 2-acetamido-3-O-(2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-oct-7-enoxyoxan-3-yl]acetamide
• CAS: 1321579-60-5
• 化学式: C₂₈H₄₉NO₁₅
• 分子量: 639.695
• InChiKey: PHIYJJDBKLWSRA-BCWOURCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  246
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  7-octen-1-yl 2-acetamido-3-O-(2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到octyl 2-acetamido-3-O-(2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and NMR studies on the ABO histo-blood group antigens: synthesis of type III and IV structures and NMR characterization of type I–VI antigens

  摘要：

  The ABO histo-blood group antigens are best known for their important roles in solid organ and bone marrow transplantation as well as transfusion medicine. Here we report the synthesis of the ABO type III and IV antigens with a 7-octen-1-yl aglycone. Also described is an NMR study of the ABO type I to VI antigens, which were carried out to probe differences in overall conformation of the molecules. These NMR investigations showed very little difference in the H-1 chemical shifts, as well as H-1-H-1 coupling constants, across all compounds, suggesting that these ABO subtypes adopt nearly identical conformations in solution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.008
• 作为产物：
  描述：

  在 甲醇 、 sodium 作用下， 以 四氢呋喃 、 氨 、 甲醇 为溶剂， 反应 2.0h， 以92%的产率得到7-octen-1-yl 2-acetamido-3-O-(2-O-(α-L-fucopyranosyl)-β-D-galactopyranosyl)-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and NMR studies on the ABO histo-blood group antigens: synthesis of type III and IV structures and NMR characterization of type I–VI antigens

  摘要：

  The ABO histo-blood group antigens are best known for their important roles in solid organ and bone marrow transplantation as well as transfusion medicine. Here we report the synthesis of the ABO type III and IV antigens with a 7-octen-1-yl aglycone. Also described is an NMR study of the ABO type I to VI antigens, which were carried out to probe differences in overall conformation of the molecules. These NMR investigations showed very little difference in the H-1 chemical shifts, as well as H-1-H-1 coupling constants, across all compounds, suggesting that these ABO subtypes adopt nearly identical conformations in solution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.008

文献信息

• Synthesis and NMR studies on the ABO histo-blood group antigens: synthesis of type III and IV structures and NMR characterization of type I–VI antigens
  作者：Peter J. Meloncelli、Lori J. West、Todd L. Lowary

  DOI：10.1016/j.carres.2011.03.008

  日期：2011.9

  The ABO histo-blood group antigens are best known for their important roles in solid organ and bone marrow transplantation as well as transfusion medicine. Here we report the synthesis of the ABO type III and IV antigens with a 7-octen-1-yl aglycone. Also described is an NMR study of the ABO type I to VI antigens, which were carried out to probe differences in overall conformation of the molecules. These NMR investigations showed very little difference in the H-1 chemical shifts, as well as H-1-H-1 coupling constants, across all compounds, suggesting that these ABO subtypes adopt nearly identical conformations in solution. (C) 2011 Elsevier Ltd. All rights reserved.