1,2-O-isopropyliden-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide | 220827-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropyliden-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide
• 英文别名: [(3aR,5S,6S,6aR)-5-[(1S)-2-amino-2-oxo-1-prop-2-enoxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] phenyl carbonate
• CAS: 220827-22-5
• 化学式: C₁₉H₂₃NO₈
• 分子量: 393.394
• InChiKey: SOYWVKXBBPYGCR-NBFUAULTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropyliden-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide 在 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 Dowex 50 W X₂ (H⁺ form) 、 水 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 8.17h， 生成 Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-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 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,2-O-isopropyliden-5-O-allyl-3-O-phenoxycarbonyl-α-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.