(S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester | 666215-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• 英文别名: benzyl (4S)-4-[[1-[6-(dimethoxymethyl)-3-(4-ethoxycarbonyl-1,3-thiazol-2-yl)pyridin-2-yl]-2-hydroxyethyl]carbamoyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 666215-54-9
• 化学式: C₃₀H₃₆N₄O₉S
• 分子量: 628.703
• InChiKey: VUOWMGVOLACGMQ-YANBTOMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  187
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 在 N-溴代丁二酰亚胺(NBS) 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 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 palladium on activated charcoal 四氧化锇 、 四(三苯基膦)钯 、 sodium azide 、 四丁基氟化铵 、 氢气 、 N-甲基吗啉氧化物 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-{1-[6-Dimethoxymethyl-3-(4-ethoxycarbonyl-thiazol-2-yl)-pyridin-2-yl]-2-hydroxy-ethylcarbamoyl}-2,2-dimethyl-oxazolidine-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