(2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one | 1064270-50-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one
• CAS: 1064270-50-3
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: ULYFBHCVBWWHIV-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 生成 (2S)-1,2-diacetoxy-3,6-dimethylheptan-4-one
  参考文献：
  名称：

  Two Unusual Carbohydrate Reactions: Nucleophilic Ring Opening of an Anhydrosugar and Reductive Elimination with Co‐occurring Hydrogenation

  摘要：

  Treatment of the 1,6-anhydrosugar epoxide 5 with a cyano-Gilman cuprate [(CuCN (6 eq.), MeLi (12 eq.)] surprisingly led to the open chain rearranged (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one (7), structurally confirmed by conversion to the corresponding diacetate 8. Another unusual reaction was found by hydrogenation of the 2-tosyl-1-bromosugar 11, leading in one operation to the twofold deoxygenated chiral pyran derivative 14. This procedure might prove to be useful in the rapid deoxygenation of sugar derivatives.

  DOI：

  10.1080/07328300802272389
• 作为产物：
  描述：

  甲基锂 、 (1S,2S,3S,4S,5R)-2-Methyl-3,4-epoxy-6,8-dioxabicyclo<3.2.1>octan-3-ol 在 CuCN 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 0.25h， 以63%的产率得到(2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one
  参考文献：
  名称：

  Two Unusual Carbohydrate Reactions: Nucleophilic Ring Opening of an Anhydrosugar and Reductive Elimination with Co‐occurring Hydrogenation

  摘要：

  Treatment of the 1,6-anhydrosugar epoxide 5 with a cyano-Gilman cuprate [(CuCN (6 eq.), MeLi (12 eq.)] surprisingly led to the open chain rearranged (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one (7), structurally confirmed by conversion to the corresponding diacetate 8. Another unusual reaction was found by hydrogenation of the 2-tosyl-1-bromosugar 11, leading in one operation to the twofold deoxygenated chiral pyran derivative 14. This procedure might prove to be useful in the rapid deoxygenation of sugar derivatives.

  DOI：

  10.1080/07328300802272389

文献信息

• Two Unusual Carbohydrate Reactions: Nucleophilic Ring Opening of an Anhydrosugar and Reductive Elimination with Co‐occurring Hydrogenation
  作者：Karsten Krohn、Ishtiaq Ahmed、Mohammed Al Sahli

  DOI：10.1080/07328300802272389

  日期：2008.8

  Treatment of the 1,6-anhydrosugar epoxide 5 with a cyano-Gilman cuprate [(CuCN (6 eq.), MeLi (12 eq.)] surprisingly led to the open chain rearranged (2S,3R)-1,2-dihydroxy-3,6-dimethylheptan-4-one (7), structurally confirmed by conversion to the corresponding diacetate 8. Another unusual reaction was found by hydrogenation of the 2-tosyl-1-bromosugar 11, leading in one operation to the twofold deoxygenated chiral pyran derivative 14. This procedure might prove to be useful in the rapid deoxygenation of sugar derivatives.