4-脱氧-DL-苏糖酸 | 105663-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-脱氧-DL-苏糖酸
• 英文名称: 4-deoxythreonic acid
• 英文别名: α-hydroxy-L-threonine；(2RS,3SR)-2,3-dihydroxybutanoic acid；Tah；2R,3S-dihydroxybutanoic acid；(+)(2R:3S)-2.3-Dihydroxy-butansaeure；L-threo-2.3-Dihydroxy-buttersaeure；4-Desoxy-L-threonsaeure；4-deoxy-L-threonic acid；(2R,3S)-2,3-dihydroxybutyric acid；(2R,3S)-2,3-dihydroxybutanoic acid
• CAS: 105663-42-1
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: LOUGYXZSURQALL-STHAYSLISA-N

物化性质

• 沸点：
  358.8±27.0 °C(Predicted)
• 密度：
  1.413±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-脱氧-DL-苏糖酸 在 αβ-dihydroxyacid dehydratase EC 4.2.1.9 of Salmonella typhimurium 作用下， 生成 3-羟基-2-氧代-丁酸
  参考文献：
  名称：

  Armstrong, Frank B.; Lipscomb, Elizabeth L.; Crout, David H. G., Journal of the Chemical Society. Perkin transactions I, 1985, p. 691 - 696

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆酸 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 仲丁醇 为溶剂， 以53%的产率得到4-脱氧-DL-苏糖酸
  参考文献：
  名称：

  Armstrong, Frank B.; Lipscomb, Elizabeth L.; Crout, David H. G., Journal of the Chemical Society. Perkin transactions I, 1985, p. 691 - 696

  摘要：

  DOI：

文献信息

• On the selectivity of oxynitrilases towards α-oxygenated aldehydes
  作者：Paola Bianchi、Gabriella Roda、Sergio Riva、Bruno Danieli、Antonina Zabelinskaja-Mackova、Herfried Griengl

  DOI：10.1016/s0040-4020(01)00054-0

  日期：2001.3

  Different α-alkoxy and α,β-di-alkoxy substituted aldehydes have been submitted to the catalytic action of the oxynitrilases from almond (PaHNL) or from Hevea brasiliensis (HbHNL), in order to explore the possibility of using these enzymes for the preparation of complex cyanohydrins. The selectivity of both enzymes towards these compounds was found to be largely dependent on the substitutents, being

  不同α -烷氧基和α，β二-烷氧基取代的醛已经被提交到醇腈的从杏仁催化作用（PaHNL）或者从巴西橡胶树（HbHNL），为了探索使用这些酶制剂的可能性复杂的氰醇。发现两种酶对这些化合物的选择性在很大程度上取决于取代基，因为醛带有在空间上更需要的苯基取代基的醛较低。违背化学添加HCN，它总是与用于形成的轻微偏爱发生的反非对映体，所述酶cyanuration存在与面部偏好，硅或再根据所使用的生物催化剂，得到氰醇的混合物，取决于起始的对映异构醛，该混合物可以富含顺式非对映异构体。
• Highly Enantioselective Reduction of Ethyl 2-Acyloxy-3-oxobutanoate with Immobilized Baker’s Yeast
  作者：Takashi Sakai、Toshiki Nakamura、Katsuyoshi Fukuda、Eiichiro Amano、Masanori Utaka、Akira Takeda

  DOI：10.1246/bcsj.59.3185

  日期：1986.10

  Reduction of ethyl 2-acetoxy-3-oxobutanoate (4a) with immobilized baker’s yeast in calcium alginate gel gave a 18 : 19 : 63 mixture of ethyl (2R,3S)- and (2S,3S)-2-acetoxy-3-hydroxybutanoates and ethyl (2S,3S)-2,3-dihydroxybutanoate each with >95% e.e. in 58% yield. A similar treatment of a 2-benzoyloxy analog of 4a afforded a 6 : 94 mixture of ethyl (2R,3S)- and (2S,3S)-2-benzoyloxy-3-hydroxybutanoates

  在藻酸钙凝胶中用固定化面包酵母还原 2-乙酰氧基-3-氧代丁酸乙酯 (4a) 得到 18:19:63 的 (2R,3S)- 和 (2S,3S)-2-乙酰氧基-3- 混合物羟基丁酸酯和 (2S,3S)-2,3-二羟基丁酸乙酯均具有 >95% ee，产率为 58%。4a 的 2-苯甲酰氧基类似物的类似处理以 70% 的收率提供了 (2R,3S)- 和 (2S,3S)-2-苯甲酰氧基-3-羟基丁酸乙酯 (>95%ee) 的 6:94 混合物。它们的绝对构型是通过与真正的 (2R,3S)- 和 (2S,3S)-2,3- 二羟基丁酸进行比较来确定的。还讨论了固定化和培养液的 pH 值对产物比的影响。
• Enantioselective sensing of insect pheromones in water
  作者：Briana L. Hickey、Junyi Chen、Yunfan Zou、Adam D. Gill、Wenwan Zhong、Jocelyn G. Millar、Richard J. Hooley

  DOI：10.1039/d1cc05540b

  日期：——

  cavitands and cationic dyes has been shown to optically sense insect pheromones at micromolar concentration in water. Machine learning approaches were used to optimize the most effective array components, which allows differentiation between small structural differences in targets, including between different diastereomers, even though the pheromones have no innate chromophore. When combined with chiral additives

  水溶性深空腔和阳离子染料的阵列组合已被证明可以在水中以微摩尔浓度光学感知昆虫信息素。机器学习方法用于优化最有效的阵列组件，即使信息素没有先天发色团，也可以区分目标的微小结构差异，包括不同的非对映异构体之间的差异。当与手性添加剂结合使用时，对映体区分是可能的，这取决于信息素的大小和形状。
• Asymmetric Dihydroxylation onto the a,b-Unsaturated Carboxylic Ester Derivatives of Camptothecin
  作者：Keiko Tagami、Shuzo Takagi、Shigeki Sano、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.3987/com-97-7892

  日期：——

  Dihydroxyalkanoic ester derivatives (4a,b) and (5a,b) of 20S-camptothecin (1) were diastereoselectively synthesized by exploiting osmium-catalyzed asymmetric dihydroxylation based on the Sharpless procedure. The absolute configuration of the newly formed chiral centers, the 2' and 3' positions of the 20-alkanoyl side chain of 4a,b and 5a,b was determined by the chemical correlation with the known chiral dihydroxyalkanoic acids.
• Complete Defluorination of 1,2,3,4-Tetramethyl-5-(trifluoromethyl)cyclopentadiene by Titanium Tetrakis(dimethylamide)—Selective Formation of a Cyclic Hexanuclear Titanium Fluoroamide and 6,6-Dimethylaminotetramethylfulvene
  作者：Cristina Santamaría、Rüdiger Beckhaus、Detlev Haase、Wolfgang Saak、Rainer Koch

  DOI：10.1002/1521-3765(20010202)7:3<622::aid-chem622>3.0.co;2-1

  日期：2001.2.2

  1,2,3,4-Tetramethyl-5-(trifluoromethyl)cyclopentadiene (Cp*(CF3)-H,1) reacts with [Ti(NMe2)(4)] (2) under mild conditions to give [Ti(mu -NMe2)(NMe2)(NMe2)(mu -F)(F)](6) (3) in nearly quantitative yield. The molecular structure of 3 consists of a ring of six [TiF2(NMe2)(2)] edge-bridged octahedra. Titanium complexes containing the Cp*(CF3) ligand, which was the primary intention of these investigations, were not observed. C5Me4=C(NMe2)(2) (4) was isolated as a by-product. The complete defluorination of an aliphatic CF3 group occurs during the reaction. The reaction mechanism involves the primary formation of a difluorofulvene intermediate C5Me4=CF2 (5), which was monitored by NMR studies. Density functional theory calculations predict a highly charged C6 atom (+ 0.87) in 5, which is discussed as the driving force of the reaction.