(4R)-4-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester | 884330-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R)-4-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R)-4-[4-[tert-butyl(dimethyl)silyl]oxy-3-oxobutyl]-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 884330-47-6
• 化学式: C₂₁H₃₉NO₆Si
• 分子量: 429.629
• InChiKey: BFPUZNDZXRFFMU-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-4-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以93%的产率得到(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-butyl]-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester
  参考文献：
  名称：

  An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins

  摘要：

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.

  DOI：

  10.1021/jo052408q
• 作为产物：
  描述：

  (4S)-2,2-dimethyl-7-(tert-butyldimethylsilanyloxymethyl)-1-oxa-3-azaspiro[4.4]non-6-ene-3-carboxylic acid tert-butyl ester 在 potassium osmate(VI) 、 sodium periodate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 168.0h， 生成 (4R)-4-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins

  摘要：

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.

  DOI：

  10.1021/jo052408q

文献信息

• An Efficient Enantioselective Synthesis of (2<i>R</i>)-Hydroxymethyl Glutamic Acid and an Approach to the (2<i>R</i>)-Hydroxymethyl-Substituted Sphingofungins
  作者：Christopher J. Hayes、Daniel M. Bradley、Nicholas M. Thomson

  DOI：10.1021/jo052408q

  日期：2006.3.31

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.