methyl 1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-5-{5-[(pyridin-2-ylthio)methyl]isoxazole-4-carbonylamino}-α-L-talofuranuronate | 1027782-32-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: methyl 1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-5-{5-[(pyridin-2-ylthio)methyl]isoxazole-4-carbonylamino}-α-L-talofuranuronate
• CAS: 1027782-32-6
• 化学式: C₂₁H₂₁N₅O₉S
• 分子量: 519.492
• InChiKey: KHXUVXHJJFFYDA-FSNPWBFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  198.87
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  (R)-uracil polyoxin C methyl ester 、 pentafluorophenyl 5-[(pyridin-2-ylthio)methyl]isoxazole-4-carboxylate 以 甲醇 为溶剂， 以238 mg的产率得到methyl 1,5-dideoxy-1-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-5-{5-[(pyridin-2-ylthio)methyl]isoxazole-4-carbonylamino}-α-L-talofuranuronate
  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