Ethyl 2-[2-[1-azido-2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-(dimethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carboxylate | 666215-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 2-[2-[1-azido-2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-(dimethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carboxylate
• CAS: 666215-52-7
• 化学式: C₂₂H₃₃N₅O₅SSi
• 分子量: 507.686
• InChiKey: UYIIMRNULLSJQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[2-[1-azido-2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-(dimethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carboxylate 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 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
• 作为产物：
  描述：

  Ethyl 2-[6-(dimethoxymethyl)-2-(trifluoromethylsulfonyloxy)pyridin-3-yl]-1,3-thiazole-4-carboxylate 在 四氧化锇 、 四(三苯基膦)钯 、 sodium azide 、 N-甲基吗啉氧化物 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 2-[2-[1-azido-2-[tert-butyl(dimethyl)silyl]oxyethyl]-6-(dimethoxymethyl)pyridin-3-yl]-1,3-thiazole-4-carboxylate
  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

文献信息

• Useful Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton of Various Thiostrepton-Type Macrocyclic Antibiotics
  作者：Chung-gi Shin、Hirofumi Saito、Yasuchika Yonezawa

  DOI：10.3987/com-03-s27

  日期：——

  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.