(4-O-acetyl-2,6-dideoxy-L-erythro-hex-1-enopyranos-3-ulos-1-yl)benzene | 142635-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (4-O-acetyl-2,6-dideoxy-L-erythro-hex-1-enopyranos-3-ulos-1-yl)benzene
• 英文别名: [(2S,3S)-2-methyl-4-oxo-6-phenyl-2,3-dihydropyran-3-yl] acetate
• CAS: 142635-22-1
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: FHUDCIJBIHKJGR-XPTSAGLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-O-acetyl-2,6-dideoxy-L-erythro-hex-1-enopyranos-3-ulos-1-yl)benzene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Palladium-mediated arylation of acetylated enones derived from glycals. 4. Synthesis of aryl-2-deoxy-.beta.-D-C-glycopyranosides

  摘要：

  The palladium-mediated arylation of the peracetylated glycal-derived enones 1, 2, and 3 afforded mixtures of C-glycosides containing an arylated enone (1a, 2a, or 3a) and an arylated ketone (1b, 2b, or 3b). A rationale for the formation of these compounds is given. Reduction of the arylated enones proceeds in a stereospecific manner, thus affording aryl 2-deoxy-beta-D-C-glycopyranosides in high yield.

  DOI：

  10.1021/jo00043a016
• 作为产物：
  描述：

  4-O-acetyl-1,5-anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose 、 苯 在 palladium diacetate 、 溶剂黄146 作用下， 反应 4.0h， 以27%的产率得到(4-O-acetyl-2,6-dideoxy-α-L-erythro-hexopyranos-3-ulos-1-yl)benzene
  参考文献：
  名称：

  Palladium-mediated arylation of acetylated enones derived from glycals. 4. Synthesis of aryl-2-deoxy-.beta.-D-C-glycopyranosides

  摘要：

  The palladium-mediated arylation of the peracetylated glycal-derived enones 1, 2, and 3 afforded mixtures of C-glycosides containing an arylated enone (1a, 2a, or 3a) and an arylated ketone (1b, 2b, or 3b). A rationale for the formation of these compounds is given. Reduction of the arylated enones proceeds in a stereospecific manner, thus affording aryl 2-deoxy-beta-D-C-glycopyranosides in high yield.

  DOI：

  10.1021/jo00043a016