tert-butyl (S)-2,4-dihydroxybutanoate | 153704-85-9

• 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)-2,4-dihydroxybutanoate
• 英文别名: tert-butyl (2S)-2,4-dihydroxybutanoate
• CAS: 153704-85-9
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: LNSYLFSLTQDSSI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2,4-dihydroxybutanoate 在 咪唑 、 草酰氯 、 sodium cyanoborohydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 tert-butyl (2S,2'S,3'S,3''S)-3'-(3''-tert-butoxycarbonyl-3''-tert-butyldimethylsilyloxypropylamino)-3'-tert-butoxycarbonyl-2'-methoxymethyloxypropyl-2-azetidinecarboxylate
  参考文献：
  名称：

  Efficient synthesis of mugineic acid, a typical phytosiderophore, utilizing the phenyl group as the carboxyl synthon

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)74778-2
• 作为产物：
  描述：

  Butanoic acid, 2,4-bis(acetyloxy)-, 1,1-dimethylethyl ester, (S)- 在 甲醇 、 水 、 三乙胺 作用下， 反应 8.0h， 以77%的产率得到tert-butyl (S)-2,4-dihydroxybutanoate
  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.
• 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.
• 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.