tert-butyl (S)-2-tert-butyldimethylsilyloxy-4-oxobutanoate | 146499-42-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (S)-2-tert-butyldimethylsilyloxy-4-oxobutanoate
• 英文别名: (S)-tert-Butyl 2-((tert-butyldimethylsilyl)oxy)-4-oxobutanoate；tert-butyl (2S)-2-[tert-butyl(dimethyl)silyl]oxy-4-oxobutanoate
• CAS: 146499-42-5
• 化学式: C₁₄H₂₈O₄Si
• 分子量: 288.459
• InChiKey: ONPPDNOABQXUDF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-tert-butyldimethylsilyloxy-4-oxobutanoate 在 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium cyanoborohydride 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.5h， 生成 (S)-1-{(S)-3-tert-Butoxycarbonyl-3-[tert-butoxycarbonyl-(3-tert-butoxycarbonyl-3-oxo-propyl)-amino]-propyl}-azetidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A New Efficient Synthesis of Nicotianamine and 2'-Deoxymugineic Acid

  摘要：

  Nicotianamine and 2'-deoxymugineic acid, phytosiderophores, have been efficiently synthesized, which will be suitable for large scale production of these plant physiologically important compounds. The synthetic method for 2',3 ''-dideoxy-3 ''-oxomugineic acid was also investigated.

  DOI：

  10.3987/com-96-s52
• 作为产物：
  描述：

  Butanoic acid, 2,4-bis(acetyloxy)-, 1,1-dimethylethyl ester, (S)- 在 四氢呋喃 、 咪唑 、 甲醇 、 草酰氯 、 水 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 tert-butyl (S)-2-tert-butyldimethylsilyloxy-4-oxobutanoate
  参考文献：
  名称：

  Total synthesis of mugineic acid. Efficient use of the phenyl group as the carboxyl synthon

  摘要：

  Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from madily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6). The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

  DOI：

  10.1016/s0040-4020(01)88039-x

文献信息

• Efficient synthesis of mugineic acid, a typical phytosiderophore, utilizing the phenyl group as the carboxyl synthon
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)74778-2

  日期：1992.12

  Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.
• Total Syntheses of Phytosiderophores, 3-Epi-Hydroxymugineic Acid, Distichonic Acid A, and 2′-Hydroxynicotianamine
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)80749-3

  日期：1994.4

  First total syntheses of the unique phytosiderophores, 3-epi-hydroxymugineic acid (2), distichonic acid A (3), and 2'-hydroxynicotianamine (5), have been efficiently achieved from the same intermediates used for the synthesis of mugineic acid (1), the typical phytosiderophore.
• Efficient synthesis of phytosiderophores, 3-epi-hydroxymugineic acid and distichonic acid A
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)74779-4

  日期：1992.12

  Synthesis of 3-epi-hydroxymugineic acid (2) and distichonic acid A (3), phytosiderophores from graminaceous plants, has been efficiently achieved for the first time.
• Total synthesis of mugineic acid. Efficient use of the phenyl group as the carboxyl synthon
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)88039-x

  日期：1993.9

  Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from madily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6). The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.
• A New Efficient Synthesis of Nicotianamine and 2'-Deoxymugineic Acid
  作者：Takayuki Shioiri、Naoko Irako、Sachiko Sakakibara、Fumiyoshi Matsuura、Yasumasa Hamada

  DOI：10.3987/com-96-s52

  日期：——

  Nicotianamine and 2'-deoxymugineic acid, phytosiderophores, have been efficiently synthesized, which will be suitable for large scale production of these plant physiologically important compounds. The synthetic method for 2',3 ''-dideoxy-3 ''-oxomugineic acid was also investigated.