Tert-butyl 2-[2-(2-acetyl-1,3-thiazol-4-yl)-6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate | 1037746-93-2

• 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: Tert-butyl 2-[2-(2-acetyl-1,3-thiazol-4-yl)-6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate
• CAS: 1037746-93-2
• 化学式: C₂₃H₂₅N₃O₅S₂
• 分子量: 487.601
• InChiKey: AXTAGJKFBIYJQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 双(乙腈)氯化钯(II) 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 以96%的产率得到Tert-butyl 2-[2-(2-acetyl-1,3-thiazol-4-yl)-6-[(2-methylpropan-2-yl)oxycarbonyl]pyridin-3-yl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics

  摘要：

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.

  DOI：

  10.1021/ol801035c

文献信息

• Highly Efficient Borylation Suzuki Coupling Process for 4-Bromo-2-ketothiazoles: Straightforward Access to Micrococcinate and Saramycetate Esters
  作者：Thibaut Martin、Claire Laguerre、Christophe Hoarau、Francis Marsais

  DOI：10.1021/ol901525t

  日期：2009.8.20

  The first palladium-catalyzed borylation of 4-bromo-2-ketothiazoles followed by a Suzuki cross-coupling reaction with haloheteroaromatics using Buchwaid's Cy-JohnPhos and XPhos ligands is reported. The methodology has allowed the fast preparation of highly valuable 4-pyridinyl- and 4-thiazolyl-2-ketothiazoles as common subunits of thiopeptide antibiotics. As direct applications, novel concise syntheses of a sulfomycinamate thio-analogue as well as micrococcinate and saramycetate esters are described.
• Direct C-2 Arylation of Alkyl 4-Thiazolecarboxylates: New Insights in Synthesis of Heterocyclic Core of Thiopeptide Antibiotics
  作者：Thibaut Martin、Cécile Verrier、Christophe Hoarau、Francis Marsais

  DOI：10.1021/ol801035c

  日期：2008.7.3

  The Pd(0)-catalyzed regioselective C-2 (hetero)arylation of tert-butyl 4-thiazolecarboxylate with a broad (hetero)aryl halide is reported, including the direct coupling of pyridinyl halides. The process has allowed the preparation of valuable 2-pyridynyl-4-thiazolecarboxylates which are components of the complex heterocyclic core of thiopeptides antibiotics. As a first application, a synthesis of a tert-butyl sulfomycinamate thio-analogue from tert-butyl 4-thiazolecarboxylate is here described through a three-step direct pyridinylation, halogenation, and Stille cross-coupling sequence.