4-methoxyphenyl (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside | 1237748-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside
• CAS: 1237748-39-8
• 化学式: C₇₄H₇₈O₁₇
• 分子量: 1239.42
• InChiKey: BJQIIVVWSGOXIN-VJOZOAKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.63
• 重原子数：
  91.0
• 可旋转键数：
  28.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  178.91
• 氢给体数：
  2.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 、 4-methoxyphenyl (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 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76%的产率得到4-methoxyphenyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->3)-(2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of a hexasaccharide present in the cell wall lipopolysaccharide of Azospirillum lipoferum Sp59b

  摘要：

  Concise chemical synthesis of a hexasaccharide repeating unit found in the cell wall lipopolysaccharide of Azospirillum lipoferum Sp59b was achieved in excellent yield. A [3+3] block synthetic strategy has been applied for the construction of the target hexasaccharide. During the synthesis, the orthogonal property of thioglycosides has been successfully exploited. Yields were high in all intermediate steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.042
• 作为产物：
  描述：

  4-methoxyphenyl (2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到4-methoxyphenyl (4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Concise synthesis of a hexasaccharide present in the cell wall lipopolysaccharide of Azospirillum lipoferum Sp59b

  摘要：

  Concise chemical synthesis of a hexasaccharide repeating unit found in the cell wall lipopolysaccharide of Azospirillum lipoferum Sp59b was achieved in excellent yield. A [3+3] block synthetic strategy has been applied for the construction of the target hexasaccharide. During the synthesis, the orthogonal property of thioglycosides has been successfully exploited. Yields were high in all intermediate steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.042