2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,4-di-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide | 220827-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,4-di-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2R,3R,4S,5S,6S)-2,5-diacetyloxy-6-carbamoyl-4-carbamoyloxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 220827-35-0
• 化学式: C₂₅H₃₅N₃O₁₇
• 分子量: 649.563
• InChiKey: YCKJXKKFSZTTFP-ARVZLBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  284
• 氢给体数：
  3
• 氢受体数：
  17

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)-1,4-di-O-acetyl-3-O-carbamoyl-α-D-glucopyranuronamide 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以95%的产率得到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
• 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 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 、 甲苯 为溶剂， 反应 76.42h， 生成 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,4-di-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