(S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester | 666215-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester
• CAS: 666215-58-3
• 化学式: C₂₈H₂₆N₄O₇S
• 分子量: 562.603
• InChiKey: DUNBQAQDJWHOCU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133.95
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester 在 对甲苯磺酸 、 溶剂黄146 作用下， 生成 2-{2-[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazol-4-yl]-6-dimethoxymethyl-pyridin-3-yl}-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-Type Macrocyclic Antibiotics

  摘要：

  A useful synthetic method for the main central 2-(2-oxazol-4-yl)-3(4-thiazol-2-yl)-6-carboxypyridine skeleton [Fragment A] constructing various thiostrepton-type macrocyclic antibiotics is described, in which the precursor of Fragment A was derived from the authentic ethyl 2-(6-dimethoxymethyl-2-trifluoromethanesulfonyloxy-3-pyridyl)thiazole-4-carboxylate in 14 steps. Finally, the fragment condensation of Fragment A with the already prepared carboxy component dipeptide [Fragment B] proceeded first to give the precursor of Fragment A-B.

  DOI：

  10.3987/com-03-s27
• 作为产物：
  描述：

  2-(6-Dimethoxymethyl-2-vinyl-pyridin-3-yl)-thiazole-4-carboxylic acid ethyl ester 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 sodium azide 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (S)-4-[3-(4-Ethoxycarbonyl-thiazol-2-yl)-6-formyl-pyridin-2-yl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid benzyl ester
  参考文献：
  名称：

  Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-Type Macrocyclic Antibiotics

  摘要：

  A useful synthetic method for the main central 2-(2-oxazol-4-yl)-3(4-thiazol-2-yl)-6-carboxypyridine skeleton [Fragment A] constructing various thiostrepton-type macrocyclic antibiotics is described, in which the precursor of Fragment A was derived from the authentic ethyl 2-(6-dimethoxymethyl-2-trifluoromethanesulfonyloxy-3-pyridyl)thiazole-4-carboxylate in 14 steps. Finally, the fragment condensation of Fragment A with the already prepared carboxy component dipeptide [Fragment B] proceeded first to give the precursor of Fragment A-B.

  DOI：

  10.3987/com-03-s27