pentafluorophenyl 3-(methylthio)-5-(pyridin-3-yl)isoxazole-4-carboxylate | 1027782-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentafluorophenyl 3-(methylthio)-5-(pyridin-3-yl)isoxazole-4-carboxylate
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 3-methylsulfanyl-5-pyridin-3-yl-1,2-oxazole-4-carboxylate；(2,3,4,5,6-pentafluorophenyl) 3-methylsulfanyl-5-pyridin-3-yl-1,2-oxazole-4-carboxylate
• CAS: 1027782-11-1
• 化学式: C₁₆H₇F₅N₂O₃S
• 分子量: 402.301
• InChiKey: ACUZYUPKSMFUCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  pentafluorophenyl 3-(methylthio)-5-(pyridin-3-yl)isoxazole-4-carboxylate 、 (S)-uracil polyoxin C methyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以286 mg的产率得到methyl (S)-2-((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)-2-(3-(methylthio)-5-(pyridin-3-yl)isoxazole-4-carboxamido)acetate
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase

  摘要：

  Stereoselective syntheses of both the natural (C5'-S) and unnatural (C5'-R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.

  DOI：

  10.1021/jo702564y
• 作为产物：
  描述：

  3-(甲硫基)-5-(吡啶-3-基)异恶唑-4-羧酸 、 五氟苯酚 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以91%的产率得到pentafluorophenyl 3-(methylthio)-5-(pyridin-3-yl)isoxazole-4-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of Novel Uracil Polyoxin C Conjugates as Substrate Analogues of Chitin Synthase

  摘要：

  Stereoselective syntheses of both the natural (C5'-S) and unnatural (C5'-R) diastereoisomers of uracil polyoxin C methyl ester have been developed. The key stereocontrolled step involves nucleophilic addition of trimethylsilyl cyanide to the appropriate chiral sulfinimine derived from 2',3'-protected 5'-formyluridine and (S)-(-)-tert-butanesulfinamide or (R)-(+)-tert-butanesulfinamide, respectively. A variety of substrate mimics designed to function as inhibitors of chitin synthase have been synthesized by conjugation of the methyl ester of uracil polyoxin C (UPOC) with activated isoxazole carboxylic acids. Amide bond formation was accomplished via coupling of the amino functionality of UPOC methyl ester with a free isoxazole acid using HBTU or alternatively an isoxazole pentafluorophenyl ester. The substrate mimics incorporate features of the nucleoside-peptide antibiotics, the polyoxins and the nikkomycins, as well as features of the transition state structure expected during polymerization of the natural chitin synthase substrate uridine diphosphoryl-N-acetylglucosamine (UDP-GlcNAc), namely, a metal-binding site and glycosyl oxocarbenium ion mimic.

  DOI：

  10.1021/jo702564y