2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide | 220827-36-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide
• CAS: 220827-36-1
• 化学式: C₂₃H₃₃N₃O₁₆
• 分子量: 607.526
• InChiKey: WSTGZTRHHHYDTK-XMWQZMJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.37
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  277.63
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide 在 铜 、 乙酰丙酮 、 锌 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-1-O-{[(R)-2-methoxycarbonyl-2-(hexyloxy)-ethoxy]-hydroxyphosphoryl}-α-D-glucopyranuronamide
  参考文献：
  名称：

  Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships

  摘要：

  Two disaccharide analogues 1b and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01063-1
• 作为产物：
  描述：

  allyl 5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide 在 四(三苯基膦)钯 吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氨 、 三正丁基氢锡 、 乙酸肼 作用下， 以 1,4-二氧六环 、 吡啶 、 N,N-二甲基乙酰胺 、 溶剂黄146 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 77.09h， 生成 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide
  参考文献：
  名称：

  Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships

  摘要：

  Two disaccharide analogues 1b and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01063-1

文献信息

• Studies on the Synthesis of Di- and Trisaccharide Analogues of Moenomycin A. Modifications in Unit E and in the Lipid Part
  作者：Guangbin Yang、Madina Mansourova、Lothar Hennig、Matthias Findeisen、Ramona Oehme、Sabine Giesa、Peter Welzel

  DOI：10.1002/hlca.200490161

  日期：2004.7

  Routes allowing the synthesis of moenomycin analogues with one modified sugar component and with new lipid parts were developed (see 10c, 12c, 16b, and 20b in Schemes 2–4). It is anticipated that such analogues will be useful for studying the mode of action of the moenomycin-type transglycosylase inhibitors in detail and for preparing analogues with improved pharmacokinetic properties.

  路由允许moenomycin类似物的合成与一种经修饰的糖组分，并用新的脂质部分被开发（见图10C，12C，16B，和20B在方案2 - 4）。预期此类类似物可用于详细研究莫能霉素型转糖基化酶抑制剂的作用方式以及用于制备具有改善的药代动力学性质的类似物。