(4R)-4-(4-hydroxy-3-oxobutyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester | 884330-50-1

• 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-(4-hydroxy-3-oxobutyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester
• 英文别名: 3-O-tert-butyl 4-O-methyl (4R)-4-(4-hydroxy-3-oxobutyl)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate
• CAS: 884330-50-1
• 化学式: C₁₆H₂₇NO₇
• 分子量: 345.393
• InChiKey: WZGDRAFGMDJDCH-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-4-(4-hydroxy-3-oxobutyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 在 四丁基碘化铵 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 170.0h， 生成 (4R)-4-[11-(2-hexyl-1,3-dioxolan-2-yl)-3-oxoundec-4-enyl]-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl 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 sodium chlorite 、 potassium osmate(VI) 、 sodium periodate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 227.5h， 生成 (4R)-4-(4-hydroxy-3-oxobutyl)-2,2-dimethyloxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl 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.