2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-methyl-α-D-glucopyranose 1-dibenzylphosphate | 732247-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-methyl-α-D-glucopyranose 1-dibenzylphosphate
• CAS: 732247-19-7
• 化学式: C₃₇H₄₂NO₉P
• 分子量: 675.716
• InChiKey: GUKVJNDDGBEAGL-LQHPVFTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-methyl-α-D-glucopyranose 1-dibenzylphosphate 在 palladium on activated charcoal 四氮唑 、 氢气 、 三乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 126.0h， 生成 uridinediphosphoryl 4-O-methyl-N-acetyl-glucosamine ammonium salt
  参考文献：
  名称：

  Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis

  摘要：

  Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1 --> 4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.014
• 作为产物：
  描述：

  3,6-di-O-benzyl-1-O-tert-butyldimethylsilyl-2-deoxy-4-O-methyl-2-phthalimido-β-D-glucopyranose 在 四丁基氟化铵 、 肼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正庚烷 、 乙基苯 为溶剂， 反应 25.25h， 生成 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-methyl-α-D-glucopyranose 1-dibenzylphosphate
  参考文献：
  名称：

  Chemical synthesis of UDP-4-O-methyl-GlcNAc, a potential chain terminator of chitin synthesis

  摘要：

  Chitin synthase converts uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc) to chitin (poly-beta-(1 --> 4)-GlcNAc). During polymerization, elongation occurs at the 4-OH (nonreducing) terminus of the growing chitin chain. Blockage of the 4-OH via incorporation of UDP-N-acetyl-4-O-methylglucosamine (UDP-4-OMe-GlcNAc, 3) can potentially terminate chitin polymerization, and represents a novel strategy for chitin synthase inhibition. The chemical synthesis of 3 and preliminary evaluation of its possible incorporation by chitin synthase are reported herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.014