(3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxo-hexopyranosyl)benzene | 100624-62-2

• 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: (3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxo-hexopyranosyl)benzene
• 英文别名: [(2R,3R,4R,6R)-3,4-diacetyloxy-6-phenyloxan-2-yl]methyl acetate
• CAS: 100624-62-2；117467-59-1；117467-60-4；117467-61-5；117467-62-6；142697-95-8；142697-96-9
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: MQWVUYXHNSQRLB-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4,6-di-O-acetyl-2-deoxy-D-threo-hex-1-enopyranos-3-ulos-1-yl)benzene 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxo-hexopyranosyl)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

文献信息

• Palladium-mediated arylation of acetylated enones derived from glycals. 4. Synthesis of aryl-2-deoxy-.beta.-D-C-glycopyranosides
  作者：Rachida Benhaddou、Stanislas Czernecki、Guy Ville

  DOI：10.1021/jo00043a016

  日期：1992.8

  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.