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-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl}-α-D-glucopyranuronamide | 220866-84-2

• 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)-4-O-acetyl-3-O-carbamoyl-1-O-{[(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl}-α-D-glucopyranuronamide
• 英文别名: methyl (2R)-3-[[(2R,3R,4S,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5-acetyloxy-6-carbamoyl-4-carbamoyloxyoxan-2-yl]oxy-(1,1,1-trichloro-2-methylpropan-2-yl)oxyphosphoryl]oxy-2-(3,8,8,11,14,18-hexamethylnonadecoxy)propanoate
• CAS: 220866-84-2
• 化学式: C₅₆H₉₅Cl₃N₃O₂₂P
• 分子量: 1299.71
• InChiKey: SWMJHHKUJLUQFL-DHQZZLGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  85
• 可旋转键数：
  43
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  338
• 氢给体数：
  3
• 氢受体数：
  22

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-1-O-{[(R)-2-methoxycarbonyl-2-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl}-α-D-glucopyranuronamide 在 铜 、 乙酰丙酮 、 锌 作用下， 以 吡啶 为溶剂， 生成 methyl (2R)-3-[[(2R,3R,4S,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-acetyloxy-6-carbamoyl-4-carbamoyloxyoxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-(3,8,8,11,14,18-hexamethylnonadecoxy)propanoate 、 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-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-hydroxy-phosphoryl}-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：

  1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosiduronamide 在 四(三苯基膦)钯 、 三乙胺 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Dowex 50 W X₂ (H⁺ form) 、 氨 、 水 、 乙酸肼 、 铜 、 溶剂黄146 、 三氟乙酸 、 锌 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 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 123.84h， 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-(3,8,8,11,14,18-hexamethyl-nonadecyloxy)-ethoxy]-(2,2,2-trichloro-1,1-dimethylethyloxy)-phosphoryl}-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