allyl 5-O-allyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide | 220827-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 5-O-allyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide
• 英文别名: [(2S,3R,4R,5R)-2-[(1S)-2-amino-2-oxo-1-prop-2-enoxyethyl]-4-hydroxy-5-prop-2-enoxyoxolan-3-yl] phenyl carbonate
• CAS: 220827-24-7
• 化学式: C₁₉H₂₃NO₈
• 分子量: 393.394
• InChiKey: VTIRJIIGEJCRSG-KCYAQADSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 5-O-allyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide 在 偶氮二异丁腈 、 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 、 乙二醇二甲醚 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 70.67h， 生成 Allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-O-allyl-3-O-carbamoyl-β-D-glucofuranosiduronamide
  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：

  D-glucurono-3,6-lactone acetonide 在 三氟甲磺酸 、 三乙胺 4-二甲氨基吡啶 、 3 A molecular sieve 、 Dowex 50 W X₂ (H⁺ form) 、 氨 、 水 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 allyl 5-O-allyl-3-O-phenoxycarbonyl-β-D-glucofuranosiduronamide
  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

• Moenomycin A: The role of the methyl group in the moenuronamide unit and a general discussion of structure-activity relationships
  作者：Naser El-Abadla、Maxime Lampilas、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller、Astrid Markus、Jean van Heijenoort

  DOI：10.1016/s0040-4020(98)01063-1

  日期：1999.1

  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.