p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside | 1453195-47-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside
• CAS: 1453195-47-5
• 化学式: C₅₁H₅₄O₁₅
• 分子量: 906.981
• InChiKey: DDCMYSKBVWZJFD-KTHYNXTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  66.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  172.97
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside 、 p-tolyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 硫酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14)

  摘要：

  Chemical synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14) is reported in the form of its p-methoxyphenyl glycosides. Suitably protected monosaccharide synthons were prepared either by literature procedure or by strategies developed in house. Stereoselective glycosylations were accomplished by the activation of thioglycosides using N-iodosuccinimide in conjunction with H2SO4-silica in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.009
• 作为产物：
  描述：

  p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.03h， 生成 p-methoxyphenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranosyl-(1→2)-6-O-benzyl-3-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14)

  摘要：

  Chemical synthesis of the trisaccharide repeating unit of the O-polysaccharide from Aeromonas hydrophila A19 (O:14) is reported in the form of its p-methoxyphenyl glycosides. Suitably protected monosaccharide synthons were prepared either by literature procedure or by strategies developed in house. Stereoselective glycosylations were accomplished by the activation of thioglycosides using N-iodosuccinimide in conjunction with H2SO4-silica in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.06.009