p-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhamnopyranoside | 1391984-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhamnopyranoside
• CAS: 1391984-93-2
• 化学式: C₃₆H₄₁N₃O₁₆
• 分子量: 771.732
• InChiKey: KKTWWZFQEQJKCB-ZUGVSJSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  55.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  235.64
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhamnopyranoside 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.07h， 以92%的产率得到p-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-4-O-benzoyl-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：

  2-azido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranoside 、 4-methoxyphenyl 3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以86%的产率得到p-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-3-O-allyloxycarbonyl-4-O-benzoyl-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