methyl 3R,4Z,6E-3-hydroxy-2,2,4-trimethyl-7-(tributylstannyl)-4,6-heptadienoate | 875577-49-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 3R,4Z,6E-3-hydroxy-2,2,4-trimethyl-7-(tributylstannyl)-4,6-heptadienoate
• 英文别名: methyl (3R,4Z,6E)-3-hydroxy-2,2,4-trimethyl-7-tributylstannylhepta-4,6-dienoate
• CAS: 875577-49-4
• 化学式: C₂₃H₄₄O₃Sn
• 分子量: 487.311
• InChiKey: QUDIPALCSHZNTE-SGFOJTIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(E)-3-iodo-2-propenyl]oxazole 、 methyl 3R,4Z,6E-3-hydroxy-2,2,4-trimethyl-7-(tributylstannyl)-4,6-heptadienoate 在 四(三苯基膦)钯 copper(l) iodide 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以100%的产率得到(R,4Z,6E,8E)-methyl 3-hydroxy-2,2,4-trimethyl-10-(oxazol-5-yl)deca-4,6,8-trienoate
  参考文献：
  名称：

  The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach

  摘要：

  The Stille coupling between a common oxazole vinyl iodide and stereodefined stannyl-diene units is described as the cornerstone of a unified synthetic route to the inthomycin family of bioactive Streptomyces metabolites. This procedure has been utilised to prepare (+)-inthomycin B and (+)-inthomycin C for the first time; in these examples the stereogenic centre was introduced using the Kiyooka ketene acetal/amino acid-derived oxazaborolidinone variant of the Mukaiyama aldol reaction. In addition, a convenient preparation of rac-inthomycin A is described based on the same strategy. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.116