methyl 5-[[(2S)-1-methoxy-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamoyl]-6-(2-prop-1-en-2-yl-1,3-oxazol-4-yl)pyridine-2-carboxylate | 618884-65-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 5-[[(2S)-1-methoxy-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamoyl]-6-(2-prop-1-en-2-yl-1,3-oxazol-4-yl)pyridine-2-carboxylate
• CAS: 618884-65-4
• 化学式: C₂₂H₂₇N₃O₇
• 分子量: 445.472
• InChiKey: BHSHDASMVHWCIY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-[[(2S)-1-methoxy-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamoyl]-6-(2-prop-1-en-2-yl-1,3-oxazol-4-yl)pyridine-2-carboxylate 在 manganese(IV) oxide 、 sodium periodate 、 四氧化锇 、 伯吉斯试剂 、 硫化氢 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.83h， 生成 dimethyl sulfomycinamate
  参考文献：
  名称：

  Synthesis of Dimethyl Sulfomycinamate

  摘要：

  Dimethyl sulfomycinamate, the oxazole-thiazole-pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin 1, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)2-oxobut-3-ynoate.

  DOI：

  10.1021/ol0357144
• 作为产物：
  描述：

  2-Isopropenyloxazole-4-carboxylic acid 在 copper(l) iodide 、 ammonium acetate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 methyl 5-[[(2S)-1-methoxy-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamoyl]-6-(2-prop-1-en-2-yl-1,3-oxazol-4-yl)pyridine-2-carboxylate
  参考文献：
  名称：

  One-Pot Multistep Bohlmann−Rahtz Heteroannulation Reactions:  Synthesis of Dimethyl Sulfomycinamate

  摘要：

  The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.

  DOI：

  10.1021/jo048106q

文献信息

• A new mild method for the one-pot synthesis of pyridines
  作者：Xin Xiong、Mark C Bagley、Krishna Chapaneri

  DOI：10.1016/j.tetlet.2004.06.061

  日期：2004.8

  Polysubstituted pyridines are prepared in good yield and with total regiocontrol by the one-pot reaction of an alkynone, 1,3-dicarbonyl compound and ammonium acetate in alcoholic solvents. This new three-component heteroannulation reaction proceeds under mild conditions in the absence of an additional acid catalyst and has been used in the synthesis of dimethyl sulfomycinamate, the acidic methanolysis

  多取代的吡啶以高收率制备，并通过炔醇，1，3-二羰基化合物和乙酸铵在醇溶剂中的一锅反应，具有完全的区域控制性。这种新的三组分杂环化反应可在温和条件下在不使用其他酸催化剂的条件下进行，已用于合成硫代肽抗生素的硫霉素家族的酸性甲醇分解降解产物二硫代丝氨酸。
• Synthesis of Dimethyl Sulfomycinamate
  作者：Mark C. Bagley、James W. Dale、Xin Xiong、Justin Bower

  DOI：10.1021/ol0357144

  日期：2003.11.1

  Dimethyl sulfomycinamate, the oxazole-thiazole-pyridine product generated in the methanolysis of the thiopeptide antibiotic sulfomycin 1, is prepared in 13 steps and 8% overall yield by the Bohlmann-Rahtz heteroannulation of 1-(oxazol-4-yl)enamines and methyl 4-(trimethylsilyl)2-oxobut-3-ynoate.
• One-Pot Multistep Bohlmann−Rahtz Heteroannulation Reactions:  Synthesis of Dimethyl Sulfomycinamate
  作者：Mark C. Bagley、Krishna Chapaneri、James W. Dale、Xin Xiong、Justin Bower

  DOI：10.1021/jo048106q

  日期：2005.2.1

  The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.