(1S)-(2-oxo-cyclohexyl)-1,2-O-isopropylidene-4,5-di-O-methyl-3-hydroxy-D-arabinitol | 937378-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-(2-oxo-cyclohexyl)-1,2-O-isopropylidene-4,5-di-O-methyl-3-hydroxy-D-arabinitol
• 英文别名: (1S)-3-deoxy-1,2-O-isopropylidene-4,5-di-O-methyl-1-[2-oxo-1-cyclohexyl]-D-arabinitol-3-one；2-[(4S,5R)-5-[(2R)-2,3-dimethoxypropanoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]cyclohexan-1-one
• CAS: 937378-73-9
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: SDHFAAWNDWFFGT-RXNXHLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-(2-oxo-cyclohexyl)-1,2-O-isopropylidene-4,5-di-O-methyl-3-hydroxy-D-arabinitol 在 正丁胺 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以60%的产率得到(2R)-1-(4,5,6,7-tetrahydrobenzofuran-2-yl)-2,3-dimethoxypropan-2-one
  参考文献：
  名称：

  Short and Efficient Synthesis of Chiral Furyl Carbinols from Carbohydrates

  摘要：

  Common sugar derivatives can be transformed in a few steps into chiral-substituted furyl carbinols. The mildness of the reaction conditions and the good yields obtained make this procedure an interesting alternative to the conventional processes.

  DOI：

  10.1021/ol070412d
• 作为产物：
  描述：

  1-环己烯氧基三甲基硅烷 在 jones' reagent 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 (1S)-(2-oxo-cyclohexyl)-1,2-O-isopropylidene-4,5-di-O-methyl-3-hydroxy-D-arabinitol
  参考文献：
  名称：

  Short and Efficient Synthesis of Chiral Furyl Carbinols from Carbohydrates

  摘要：

  Common sugar derivatives can be transformed in a few steps into chiral-substituted furyl carbinols. The mildness of the reaction conditions and the good yields obtained make this procedure an interesting alternative to the conventional processes.

  DOI：

  10.1021/ol070412d

文献信息

• Efficient Conversion of Carbohydrates into 1-<i>C</i>-Alditols: Application to the Synthesis of Chiral γ-Substituted Butenolides and Bicyclic Alkaloid Analogues
  作者：Alicia Boto、Dácil Hernández、Rosendo Hernández

  DOI：10.1021/jo800478a

  日期：2008.7.1

  steps into valuable, more complex products. The tandem radical scission of carbohydrates−oxidation reaction gave acetoxy acetals, which were converted into a variety of chiral C-alditols in good global yields and excellent 1,2-trans stereoselectivity. The reaction was the key step in the synthesis of hydroxylated γ-substituted butenolides and bicyclic alkaloid analogues.

  现成的糖衍生物只需几步即可转化为有价值的，更复杂的产品。碳水化合物的串联自由基断裂-氧化反应产生了乙酰氧基缩醛，该乙酰氧基缩醛以良好的总体收率和优异的1,2-反式立体选择性被转化为多种手性C-醛糖醇。该反应是合成羟基化的γ-取代的丁烯内酯和双环生物碱类似物的关键步骤。
• Short and Efficient Synthesis of Chiral Furyl Carbinols from Carbohydrates
  作者：Alicia Boto、Dácil Hernández、Rosendo Hernández

  DOI：10.1021/ol070412d

  日期：2007.4.1

  Common sugar derivatives can be transformed in a few steps into chiral-substituted furyl carbinols. The mildness of the reaction conditions and the good yields obtained make this procedure an interesting alternative to the conventional processes.