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 | 1391984-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 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
• CAS: 1391984-99-8
• 化学式: C₅₆H₅₇Cl₃N₂O₂₁
• 分子量: 1200.43
• InChiKey: NTDVYOPXDMWHKZ-RBIRJYIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  82.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  292.43
• 氢给体数：
  2.0
• 氢受体数：
  22.0

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-azido-2-deoxy-α-D-mannopyranosyl-(1→2)-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-]4-O-benzoyl-α-L-rhamnopyranoside 在 吡啶 、 ammonium cerium (IV) nitrate 、 palladium on activated charcoal 、 水 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0~30.0 ℃ 、101.33 kPa 条件下， 反应 16.83h， 生成 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
  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