p-methoxyphenyl 2-acetamido-2-deoxy-α-D-mannopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)-]α-L-rhamnopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside | 1391984-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2-acetamido-2-deoxy-α-D-mannopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)-]α-L-rhamnopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside
• 英文别名: ManNAc(a1-2)[Rha(a1-3)]Rha(a1-4)GlcNAc(b1-3)Rha(a)-O-Ph(4-OMe)；N-[(2R,3S,4R,5S,6R)-2-[(2S,3R,4R,5S,6S)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-2-(4-methoxyphenoxy)-6-methyloxan-4-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-5-hydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1391984-97-6
• 化学式: C₄₁H₆₄N₂O₂₄
• 分子量: 968.958
• InChiKey: BMSAPISDROJQNS-ZOCPOREPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  67
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  382
• 氢给体数：
  13
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  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 在 甲醇 、 氨 作用下， 反应 168.0h， 以89%的产率得到p-methoxyphenyl 2-acetamido-2-deoxy-α-D-mannopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)-]α-L-rhamnopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-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