p-methoxyphenyl (4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside | 1610701-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS: 1610701-74-0
• 化学式: C₆₈H₆₉NO₁₆
• 分子量: 1156.29
• InChiKey: DGQBBWVPSQTBCG-AMHWMLFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.54
• 重原子数：
  85.0
• 可旋转键数：
  21.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  177.6
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 、 ethyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以76%的产率得到p-methoxyphenyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13

  摘要：

  Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O13 strain has been achieved using a straightforward linear synthetic strategy. Similar reaction conditions have been used for all glycosylations as well as protective group manipulations. All intermediate steps are high yielding and the glycosylation steps are stereoselective. The synthesized pentasaccharide was subjected to conformational analysis using 2D ROESY NMR spectral analysis and molecular dynamics (MD) simulation to get detailed information on conformation of the molecule in aqueous solution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.012
• 作为产物：
  描述：

  p-methoxyphenyl (3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到p-methoxyphenyl (4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Linear synthesis and conformational analysis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O13

  摘要：

  Synthesis of the pentasaccharide repeating unit of the O-antigen of Escherichia coli O13 strain has been achieved using a straightforward linear synthetic strategy. Similar reaction conditions have been used for all glycosylations as well as protective group manipulations. All intermediate steps are high yielding and the glycosylation steps are stereoselective. The synthesized pentasaccharide was subjected to conformational analysis using 2D ROESY NMR spectral analysis and molecular dynamics (MD) simulation to get detailed information on conformation of the molecule in aqueous solution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.03.012