p-methoxyphenyl 3-O-acetyl-4-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-acetyl-α-L-rhamnopyranoside | 1391984-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3-O-acetyl-4-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-acetyl-α-L-rhamnopyranoside
• CAS: 1391984-98-7
• 化学式: C₃₄H₄₁NO₁₅
• 分子量: 703.697
• InChiKey: YJFQWPBFNMBQGA-PJYHKFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200.68
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-mannopyranosyl-(1→2)-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-]4-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 、 p-methoxyphenyl 3-O-acetyl-4-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-acetyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以69%的产率得到p-methoxyphenyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-mannopyranosyl-(1→2)-[2,3,4-tri-O-benzoyl-α-l-rhamnopyranosyl-(1→3)-]4-O-benzoyl-α-L-rhamnopyranosyl-(1→4)-3-O-acetyl-4-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and plant growth regulation activity of α-d-ManpNAc-(1→2)-[α-l-Rhap-(1→3)-]α-l-Rhap-(1→4)-β-d-GlupNAc-(1→3)-α-l-Rhap, the repeating unit of O-antigen of Rhizobium trifolii 4s

  摘要：

  The synthesis of a pentasaccharide 2 containing acetamido-2-deoxy-D-glucose and acetamido-2-deoxy-D-mannose related to the cell wall polysaccharide of Rhizobium trifolii 4s has been achieved by a [2+3] approach from commercially available L-rhamnose, D-glucose, and D-glucosamine as the starting materials. The target molecule was equipped with a p-methoxylphenyl handle at the reducing terminus to allow for further glycoconjugate formation via selective cleavage of this group. The bioassay suggested that the synthetic pentasaccharide 2 can stimulate the growth of wheat coleoptile similarly to indole-3-acetic acid (IAA), and promote the wheat seedling development before winter by seed treatment at a concentration of 20 mg/L. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.006
• 作为产物：
  描述：

  p-methoxyphenyl 3,4,6-tri-O-acetyl-2-phthalimido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 甲醇 、 对甲苯磺酸 、 一水合肼 、 溶剂黄146 、 乙酰氯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.0h， 生成 p-methoxyphenyl 3-O-acetyl-4-O-benzoyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-2,4-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and plant growth regulation activity of α-d-ManpNAc-(1→2)-[α-l-Rhap-(1→3)-]α-l-Rhap-(1→4)-β-d-GlupNAc-(1→3)-α-l-Rhap, the repeating unit of O-antigen of Rhizobium trifolii 4s

  摘要：

  The synthesis of a pentasaccharide 2 containing acetamido-2-deoxy-D-glucose and acetamido-2-deoxy-D-mannose related to the cell wall polysaccharide of Rhizobium trifolii 4s has been achieved by a [2+3] approach from commercially available L-rhamnose, D-glucose, and D-glucosamine as the starting materials. The target molecule was equipped with a p-methoxylphenyl handle at the reducing terminus to allow for further glycoconjugate formation via selective cleavage of this group. The bioassay suggested that the synthetic pentasaccharide 2 can stimulate the growth of wheat coleoptile similarly to indole-3-acetic acid (IAA), and promote the wheat seedling development before winter by seed treatment at a concentration of 20 mg/L. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.12.006