[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(5-bromo-2-methoxyphenoxy)oxan-2-yl]methyl acetate | 163852-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(5-bromo-2-methoxyphenoxy)oxan-2-yl]methyl acetate
• CAS: 163852-97-9
• 化学式: C₂₁H₂₅BrO₁₁
• 分子量: 533.327
• InChiKey: NMGKTUUUWIDGJB-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-戊烯酸乙酯 、 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(5-bromo-2-methoxyphenoxy)oxan-2-yl]methyl acetate 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 反应 24.0h， 生成 ethyl (E)-5-[4-methoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]pent-4-enoate 、 ethyl 4-[4-methoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]pent-4-enoate
  参考文献：
  名称：

  Regioselective bromination of O-β-glycosylated aromatics

  摘要：

  The quasi quantitative and regioselective bromination of O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) phenols is described. The orientating effect of the glycoside group is compared with those of other oxygenated groups and its usefulness illustrated with examples. These bromo-glycoslyated aromatics are able to react with alkenes via a Heck reaction and could be used for the synthesis of natural products.

  DOI：

  10.1016/0040-4039(95)00050-m
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 在 sodium hydroxide 、 苄基三乙基氯化铵 、 溴 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(5-bromo-2-methoxyphenoxy)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Regioselective bromination of O-β-glycosylated aromatics

  摘要：

  The quasi quantitative and regioselective bromination of O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) phenols is described. The orientating effect of the glycoside group is compared with those of other oxygenated groups and its usefulness illustrated with examples. These bromo-glycoslyated aromatics are able to react with alkenes via a Heck reaction and could be used for the synthesis of natural products.

  DOI：

  10.1016/0040-4039(95)00050-m