(R)-N-((E)-((2R,3R,4R,5R)-5-(3-benzyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)methylene)-2-methylpropane-2-sulfinamide | 1027782-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-((E)-((2R,3R,4R,5R)-5-(3-benzyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)methylene)-2-methylpropane-2-sulfinamide
• CAS: 1027782-23-5
• 化学式: C₃₄H₃₇N₃O₆S
• 分子量: 615.75
• InChiKey: IUBJSAODNHONJZ-KOEUBEMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101.12
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-N-((E)-((2R,3R,4R,5R)-5-(3-benzyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)methylene)-2-methylpropane-2-sulfinamide 、 三甲基氰硅烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成
  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：

  (2S,3S,4R,5R)-5-(3-benzyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis(benzyloxy)tetrahydrofuran-2-carbaldehyde 、 (R)-(+)-叔丁基亚磺酰胺 在 copper(I) sulfate 、 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到(R)-N-((E)-((2R,3R,4R,5R)-5-(3-benzyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)methylene)-2-methylpropane-2-sulfinamide
  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