2-{2-[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazol-4-yl]-6-dimethoxymethyl-pyridin-3-yl}-thiazole-4-carboxylic acid ethyl ester | 666215-60-7

• 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: 2-{2-[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazol-4-yl]-6-dimethoxymethyl-pyridin-3-yl}-thiazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2-[6-(dimethoxymethyl)-2-[2-[(1S)-2-hydroxy-1-(phenylmethoxycarbonylamino)ethyl]-1,3-oxazol-4-yl]pyridin-3-yl]-1,3-thiazole-4-carboxylate
• CAS: 666215-60-7
• 化学式: C₂₇H₂₈N₄O₈S
• 分子量: 568.607
• InChiKey: KHOWAMZNCSIENA-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  183
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-{2-[2-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazol-4-yl]-6-dimethoxymethyl-pyridin-3-yl}-thiazole-4-carboxylic acid ethyl ester 在 palladium on activated charcoal 咪唑 、 (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexa.. 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 benzyl (4S)-4-[4-[[(2S)-3-[tert-butyl(diphenyl)silyl]oxy-1-[[(1S)-2-[tert-butyl(diphenyl)silyl]oxy-1-[4-[6-(dimethoxymethyl)-3-(4-ethoxycarbonyl-1,3-thiazol-2-yl)pyridin-2-yl]-1,3-oxazol-2-yl]ethyl]amino]-1-oxopropan-2-yl]carbamoyl]-5-methyl-1,3-oxazol-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-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
• 作为产物：
  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