allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(3-(trifluoromethyl)-benzoyl)-α-D-galactopyranosiduronamide | 220974-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(3-(trifluoromethyl)-benzoyl)-α-D-galactopyranosiduronamide
• 英文别名: [(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-carbamoyl-4-carbamoyloxy-6-prop-2-enoxyoxan-3-yl] 3-(trifluoromethyl)benzoate
• CAS: 220974-57-2
• 化学式: C₃₂H₃₈F₃N₃O₁₆
• 分子量: 777.659
• InChiKey: SXALSERNPYYTOG-VDVIJNNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  266.63
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(3-(trifluoromethyl)-benzoyl)-α-D-galactopyranosiduronamide 在 magnesium(II) perchlorate 作用下， 以 水 、 异丙醇 为溶剂， 反应 48.0h， 以95%的产率得到allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-deoxy-α-D-xylo-hexopyranosiduronamide
  参考文献：
  名称：

  Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F

  摘要：

  A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01225-3
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3R,4S,5R,6S)-2-allyloxy-6-carbamoyl-5-hydroxy-4-trichloromethylcarbamoyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester 在 吡啶 、 锌 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 allyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-carbamoyl-4-O-(3-(trifluoromethyl)-benzoyl)-α-D-galactopyranosiduronamide
  参考文献：
  名称：

  Synthesis and transglycosylase-inhibiting properties of a disaccharide analogue of moenomycin A lacking substitution at C-4 of unit F

  摘要：

  A disaccharide analogue (A4 = 13c) of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01225-3