diethyl C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate | 648431-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: diethyl C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate
• CAS: 648431-77-0
• 化学式: C₂₀H₃₀NO₈P
• 分子量: 443.434
• InChiKey: BXWDNLGRMKZXPC-DAUOMPHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 diethyl 4'-O-methyl-α-L-rhamnopyranosyl-(1->3)-C-(2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate
  参考文献：
  名称：

  Analogues of the mycobacterial arabinogalactan linkage disaccharide as cell wall biosynthesis inhibitors

  摘要：

  The mycobacterial arabinogalactan linkage disaccharide [alpha-(L)-Rha-(1 --> 3)-alpha-D-GlcNAc] provides a basis for the design of new antitubercular drugs, since it supports a key skeletal structure in the bacterial cell wall. A series of analogues of the linker was synthesized by coupling appropriate thiorhamnosyl donors modified at their 4-positions, with an N-acetyl glucosamine acceptor. In a cell-free enzyme inhibition assay, three analogues inhibited the activity of the galactosyltransferase that adds a Galf residue to the linkage disaccharide. Although the compounds were modest inhibitors, these data confirm the viability of this approach to anti-mycobacterial agents. It is especially significant that the three effective compounds are modified at the site of the acceptor atom in the natural substrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00366-3
• 作为产物：
  描述：

  diethyl C-(2-acetamido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)methanephosphonate 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 diethyl C-(4,6-O-benzylidene-2-acetamido-2-deoxy-α-D-glucopyranosyl)methanephosphonate
  参考文献：
  名称：

  Analogues of the mycobacterial arabinogalactan linkage disaccharide as cell wall biosynthesis inhibitors

  摘要：

  The mycobacterial arabinogalactan linkage disaccharide [alpha-(L)-Rha-(1 --> 3)-alpha-D-GlcNAc] provides a basis for the design of new antitubercular drugs, since it supports a key skeletal structure in the bacterial cell wall. A series of analogues of the linker was synthesized by coupling appropriate thiorhamnosyl donors modified at their 4-positions, with an N-acetyl glucosamine acceptor. In a cell-free enzyme inhibition assay, three analogues inhibited the activity of the galactosyltransferase that adds a Galf residue to the linkage disaccharide. Although the compounds were modest inhibitors, these data confirm the viability of this approach to anti-mycobacterial agents. It is especially significant that the three effective compounds are modified at the site of the acceptor atom in the natural substrate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00366-3