(4R,4'R,5'S,2'E)-3-[5'-hydroxy-2',4'-dimethyl-2'-hexenoyl]-4-isopropyl-1,3-oxazolidin-2-one | 1044263-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,4'R,5'S,2'E)-3-[5'-hydroxy-2',4'-dimethyl-2'-hexenoyl]-4-isopropyl-1,3-oxazolidin-2-one
• 英文别名: (4R)-3-[(E,4R,5S)-5-hydroxy-2,4-dimethylhex-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1044263-60-6
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: YYNOHHLJULGSST-DDHADCDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙醛 、 (4R,1'E,3'E)-(-1'-{[tert-butyl(dimethyl)silyl]oxy}-2'-methyl-1',3'-pentadienyl)-4-isopropyl-1,3-oxazolidin-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以74%的产率得到(4R,4'R,5'S,2'E)-3-[5'-hydroxy-2',4'-dimethyl-2'-hexenoyl]-4-isopropyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Concise route to defined stereoisomers of the hydroxy acid of the chondramides

  摘要：

  The use of Kobayashi vinylogous aldol reaction in the reaction with acetaldehyde led to anti-aldol product 11. After reductive removal of the chiral auxiliary, the primary alcohol was converted to the allyliodide 14. This compound could be engaged in an Evans alkylation reaction, leading eventually to hydroxy acid 19. Inclusion of a Mitsunobu inversion reaction on the sequence starting with ent-11 led to hydroxy ester 30, featuring a 6,7-syn-configuration. These hydroxy acids should help to elucidate the correct stereostructure of the chondramide depsipeptides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.109