methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-β-D-mannopyranosyl-(1->4)-α-D-mannopyranoside | 1225486-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-β-D-mannopyranosyl-(1->4)-α-D-mannopyranoside
• 英文别名: GlcNAc(b1-4)GlcNAc(b1-4)Man(b1-4)a-Man1Me；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-6-[(2R,3S,4R,5S,6S)-6-[(2R,3S,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1225486-40-7
• 化学式: C₂₉H₅₀N₂O₂₁
• 分子量: 762.717
• InChiKey: LKQDAVUAHFESMU-YJCUBTLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以65.5 mg的产率得到methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-β-D-mannopyranosyl-(1->4)-α-D-mannopyranoside
  参考文献：
  名称：

  Convergent synthesis of the tetrasaccharide repeating unit related to the O-antigenic polysaccharide of Escherichia coli 78

  摘要：

  A convergent synthesis of the tetrasaccharide repeating unit of the O-antigenic cell wall polysaccharide of Escherichia coli 78, as the corresponding methyl glycoside (I), is being reported. It involved stereoselective glycosidation of a beta-linked mannodisaccharide acceptor with a beta-linked glucosamine based disaccharide thioglycoside donor, which were prepared from the corresponding functionalised monosaccharide based glycosyl donors and acceptors. The resulting tetrasaccharide derivative was finally converted to (I) by selective deprotection and also by global protection and deprotection techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.052