(4R)-4-(2-carboxyethyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R)-4-(2-carboxyethyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester
• 英文别名: (4R)-4-(2-carboxyethyl)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidine-4-carboxylic acid
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: CJXBVPKADSNRDD-CQSZACIVSA-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：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-4-(2-carboxyethyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 19.0h， 以21.8 mg的产率得到(2R)-2-amino-2-(hydroxymethyl)pentanedioic acid
  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 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以88%的产率得到(4R)-4-(2-carboxyethyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester
  参考文献：
  名称：

  从羟甲基谷氨酸 (HMG) 对映选择性形式合成 (+)-Lactacystin

  摘要：

  由羟甲基谷氨酸 (HMG) 正式合成 (+)-lactacystin，并使用亚烷基卡宾插入反应构建关键的含氮季铵中心。我们的路线在高级吡咯烷酮中间体处拦截了 Shibasaki 的路线，从中可以按照 Donohoe 的路线完成合成。

  DOI：

  10.1055/s-0029-1219207

文献信息

• An Enantioselective Formal Synthesis of (+)-Lactacystin from Hydroxymethyl Glutamic Acid (HMG)
  作者：Christopher Hayes、Abdul Hameed、Alexander Blake

  DOI：10.1055/s-0029-1219207

  日期：2010.3

  A formal synthesis of (+)-lactacystin from hydroxymethylglutamic acid (HMG), with an alkylidene carbene insertion reaction being used to construct the key nitrogen-bearing quaternary centre has been completed. Our route intercepts that of Shibasaki at an advanced pyrrolidinone intermediate, from which the synthesis can be completed following Donohoe's route.

  由羟甲基谷氨酸 (HMG) 正式合成 (+)-lactacystin，并使用亚烷基卡宾插入反应构建关键的含氮季铵中心。我们的路线在高级吡咯烷酮中间体处拦截了 Shibasaki 的路线，从中可以按照 Donohoe 的路线完成合成。
• 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.