(1R)-1-(2-oxo-2-phenylethyl)-3-O-formyl-1,2-O-isopropylidene-4-O-methyl-D-erythritol | 937378-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-(2-oxo-2-phenylethyl)-3-O-formyl-1,2-O-isopropylidene-4-O-methyl-D-erythritol
• 英文别名: (1R)-(2-oxo-2-phenylethyl)-1,2-O-isopropylidine-3-O-formyl-4-O-methyl-D-erythritol；[(1R)-1-[(4S,5R)-2,2-dimethyl-5-phenacyl-1,3-dioxolan-4-yl]-2-methoxyethyl] formate
• CAS: 937378-68-2
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: BOKNYYOQOUDCOJ-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (1R)-1-(2-oxo-2-phenylethyl)-3-O-formyl-1,2-O-isopropylidene-4-O-methyl-D-erythritol 在 碳酸氢钠 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以74%的产率得到(1R)-2-methoxy-1-(5-phenylfuran-2-yl)ethanol
  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-O-acetyl-3-O-formyl-1,2-isopropylidene-4-O-methyl-D-erythritol 、 1-苯基-1-三甲基硅氧乙烯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(1R)-1-(2-oxo-2-phenylethyl)-3-O-formyl-1,2-O-isopropylidene-4-O-methyl-D-erythritol
  参考文献：
  名称：

  碳水化合物到1- C-醛糖醇的有效转化：在手性γ-取代的丁烯内酯和双环生物碱类似物的合成中的应用

  摘要：

  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。

  DOI：

  10.1021/jo800478a

文献信息

• Synthesis of acyclic nucleosides and other C-1 substituted alditols from carbohydrates using a tandem alkoxyl radical β-fragmentation–nucleophilic addition
  作者：Alicia Boto、Rosendo Hernández、Ernesto Suárez

  DOI：10.1016/s0040-4039(01)02016-0

  日期：2001.12

  The oxidative beta -fragmentation of alkoxyl radicals generated from easily available carbohydrates is an efficient methodology to obtain acyclic nucleosides and other C-1 substituted alditols. In the reaction conditions an oxycarbenium ion is generated, which can be trapped by a variety of oxygen, carbon and nitrogen nucleophiles, in good yields and stereoselectivities. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.