ethyl (2S,3R)-2,3-dihydroxy-3-(4-nitrophenyl)propanoate | 142917-83-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (2S,3R)-2,3-dihydroxy-3-(4-nitrophenyl)propanoate
• CAS: 142917-83-7
• 化学式: C₁₁H₁₃NO₆
• 分子量: 255.227
• InChiKey: OQPPQWYOCYMINO-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R)-2,3-dihydroxy-3-(4-nitrophenyl)propanoate 在 titanium(IV) isopropylate 、 sodium hydroxide 、 sodium tetrahydroborate 、 二正丁基氧化锡 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 氯霉素
  参考文献：
  名称：

  环状亚氨基碳酸酯重排的合成应用：氯霉素和4- epi- cytoxazone的对映选择性合成

  摘要：

  使用不对称二羟基化和环状亚氨基碳酸酯重排作为关键步骤，对映体选择性合成了氯霉素和4-表-胞cyto酮。

  DOI：

  10.1016/s0040-4039(00)00878-9
• 作为产物：
  描述：

  (1S,5S,8S,9R)-9-(4-Nitro-phenyl)-5-phenyl-3,10,11-trioxa-6-aza-tricyclo[6.2.1.0^1,6]undecan-7-one 在 lithium hydroxide 、 三甲基氯硅烷 、 水 、 双氧水 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 ethyl (2S,3R)-2,3-dihydroxy-3-(4-nitrophenyl)propanoate
  参考文献：
  名称：

  Highly selective chirally templated isomünchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-dihydroxyacid

  摘要：

  Additions of p-nitro- and p-methoxybenzaldehyde to isomunchnone derivatives of (5S)-phenyloxazin-3-one and -2,3-dione led to corresponding adducts (3,4,6) with excellent diastereofacial and exo-selectivity, Hydrolysis and subsequent cleavage of adduct 3 permitted recovery of the original template and furnished dihydroxyacid 9 that was transformed into the known ethyl ester 10. Comparison of its optical rotation with the literature value confirmed its high optical purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00919-2

文献信息

• Asymmetric synthesis of chloramphenicol
  作者：A. V. Rama Rao、S. Prahlada Rao、Manjunath N. Bhanu

  DOI：10.1039/c39920000859

  日期：——

  Enantioselective synthesis of chloramphenicol is described by a route using (2S,3R)-4-nitrophenylglycidol.

  采用(2S,3R)-4-硝基苯基缩水甘油醇路线，描述了氯霉素的对映选择性合成。
• Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO ₂ ) Donors
  作者：Satish R. Malwal、Kundansingh A. Pardeshi、Harinath Chakrapani

  DOI：10.1002/cbic.201900614

  日期：2020.4.17

  Although sulfur dioxide (SO2 ) finds widespread use in the food industry as its hydrated sulfite form, a number of aspects of SO2 biology remain to be completely understood. Of the tools available for intracellular enhancement of SO2 levels, most suffer from poor cell permeability and a lack of control over SO2 release. We report 1,2-cyclic sulfite diesters as a new class of reliable SO2 donors that

  尽管二氧化硫（SO2）以其水合亚硫酸盐形式在食品工业中得到广泛使用，但SO2生物学的许多方面仍有待完全理解。在可用于细胞内提高SO2水平的工具中，大多数工具的细胞通透性较差，并且缺乏对SO2释放的控制。我们报告1,2-环亚硫酸盐二酯为一类新的可靠的SO2供体，其通过亲核置换在缓冲液中解离以产生具有可调释放曲线的SO2。我们提供的数据支持这些SO2供体比亚硫酸氢钠（细胞研究中最常用的SO2供体）更有效地提高细胞内SO2水平的适用性。
• Synthetic applications of the cyclic iminocarbonate rearrangement: enantioselective syntheses of chloramphenicol and 4-epi-cytoxazone
  作者：Jung Nam Park、Soo Y. Ko、Hun Y. Koh

  DOI：10.1016/s0040-4039(00)00878-9

  日期：2000.7

  Chloramphenicol and 4-epi-cytoxazone have been enantioselectively synthesized using the asymmetric dihydroxylation and the cyclic iminocarbonate rearrangement as key steps.

  使用不对称二羟基化和环状亚氨基碳酸酯重排作为关键步骤，对映体选择性合成了氯霉素和4-表-胞cyto酮。
• Highly selective chirally templated isomünchnone cycloadditions of achiral aldehydes: Synthesis of an enantiopure α,β-dihydroxyacid
  作者：Michael G.B Drew、Marion Fengler-Veith、Laurence M Harwood、Archie W Jahans

  DOI：10.1016/s0040-4039(97)00919-2

  日期：1997.6

  Additions of p-nitro- and p-methoxybenzaldehyde to isomunchnone derivatives of (5S)-phenyloxazin-3-one and -2,3-dione led to corresponding adducts (3,4,6) with excellent diastereofacial and exo-selectivity, Hydrolysis and subsequent cleavage of adduct 3 permitted recovery of the original template and furnished dihydroxyacid 9 that was transformed into the known ethyl ester 10. Comparison of its optical rotation with the literature value confirmed its high optical purity. (C) 1997 Elsevier Science Ltd.