4-methoxyphenyl (3,4-di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside | 1239880-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (3,4-di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
• CAS: 1239880-54-6
• 化学式: C₃₈H₃₈N₄O₁₃
• 分子量: 758.739
• InChiKey: PLEFJCOEAKYHRR-UVSRZOKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  55.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  203.35
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (3,4-di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Convergent synthesis of a common pentasaccharide-repeating unit corresponding to the O-specific polysaccharide of Escherichia coli O4:K3, O4:K6, and O4:K12

  摘要：

  A convergent chemical synthesis of a pentasaccharide found in the O-specific polysaccharide of Escherichia coli O4.K3, O4:K6, and O4:K12 has been achieved in excellent yield. A [3+2] block synthetic strategy has been adopted to couple a disaccharide donor 11 with a trisaccharide acceptor 10 for the construction of the pentasaccharide derivative 12 which on deprotection furnished target pentasaccharide 1 as its 4-methoxyphenyl glycoside Disaccharide thioglycoside donor 11 and trisaccharide acceptor 10 were prepared from suitably protected monosaccharide intermediates Yields were excellent in all steps. (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.056
• 作为产物：
  描述：

  (2S,3R,4S,5S)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 p-Methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以73%的产率得到4-methoxyphenyl (3,4-di-O-acetyl-2-azido-2-deoxy-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Convergent synthesis of a common pentasaccharide-repeating unit corresponding to the O-specific polysaccharide of Escherichia coli O4:K3, O4:K6, and O4:K12

  摘要：

  A convergent chemical synthesis of a pentasaccharide found in the O-specific polysaccharide of Escherichia coli O4.K3, O4:K6, and O4:K12 has been achieved in excellent yield. A [3+2] block synthetic strategy has been adopted to couple a disaccharide donor 11 with a trisaccharide acceptor 10 for the construction of the pentasaccharide derivative 12 which on deprotection furnished target pentasaccharide 1 as its 4-methoxyphenyl glycoside Disaccharide thioglycoside donor 11 and trisaccharide acceptor 10 were prepared from suitably protected monosaccharide intermediates Yields were excellent in all steps. (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.056