(-)-polyoxamic acid | 41325-39-7

• 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: (-)-polyoxamic acid
• 英文别名: (2R,3R,4R)-2-amino-3,4,5-trihydroxypentanoic acid
• CAS: 41325-39-7
• 化学式: C₅H₁₁NO₅
• 分子量: 165.146
• InChiKey: LYCRDZDACLCUCZ-JJYYJPOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-polyoxamic acid 、 乙酸酐 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到2-acetamido-2-deoxy-D-xylono-1,4-lactone
  参考文献：
  名称：

  Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques

  摘要：

  Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00410-5
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 palladium on activated charcoal 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.25h， 生成 (-)-polyoxamic acid
  参考文献：
  名称：

  使用2,3-叠氮基-γ-内酯方法合成（-）-聚草氨酸的对映体全合成。

  摘要：

  由2，3-叠氮基-γ-内酯7分六步合成聚草酰胺酸的非天然对映体，总收率为10％。该策略的关键步骤是氮丙啶环向亲核开环活化所需的氮丙啶环氮原子上的脱保护-保护序列。

  DOI：

  10.1021/jo035039b

文献信息

• Double diastereocontrol in the synthesis of enantiomerically pure polyoxamic acid
  作者：Laurence M. Harwood、Sarah M. Robertson

  DOI：10.1039/a807471b

  日期：——

  Polyoxamic acid 4 is prepared by a short and efficient process involving diastereochemically matched cycloaddition of 5-(S)-phenylmorpholin-2-one 1 with (S)-glyceraldehyde acetonide 2, followed by sequential hydrolysis and hydrogenolysis of the adduct.

  聚氧肟酸 4 的制备过程简短而高效，先将 5-(S)-苯基吗啉-2-酮 1 与 (S)- 乙醛缩丙酮 2 进行非对映化学匹配环加成，然后依次对加成物进行水解和氢解。
• Total Synthesis of (+)-Polyoxamic Acid via Visible-Light-Mediated Photocatalytic β-Scission and 1,5-Hydrogen Atom Transfer of Glucose Derivative
  作者：Takuro Matsuoka、Shinsuke Inuki、Takashi Miyagawa、Shinya Oishi、Hiroaki Ohno

  DOI：10.1021/acs.joc.0c00910

  日期：2020.6.19

  A total synthesis of polyoxamic acid has been achieved. The key feature of the synthetic route is a visible-light-mediated β-scission and carbon-to-carbon 1,5-hydrogen atom transfer (1,5-HAT) to provide the functionalized alditol under mild conditions. This type of carbon-to-carbon 1,5-HAT initiated by C(sp3)-centered radicals has been scarcely reported. Furthermore, the reaction was adapted for flow

  已经实现了聚草酰胺酸的全合成。合成路线的关键特征是可见光介导的β断裂和碳-碳1,5-氢原子转移（1,5-HAT），可在温和条件下提供官能化的糖醇。由C（sp 3）为中心的自由基引发的这种碳-碳1,5-HAT的报道很少。此外，该反应适用于流化学，促进了聚草酰胺酸的全合成。
• Bols, Mikael; Lundt, Inge, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 67 - 74
  作者：Bols, Mikael、Lundt, Inge

  DOI：——

  日期：——
• A straightforward route to the asymmetric synthesis of 3,4-diepipolyoxamic acid and its isomers
  作者：Shuo Li、Xin-Ping Hui、Shao-Bo Yang、Zhong-Jian Jia、Peng-Fei Xu、Ta-Jung Lu

  DOI：10.1016/j.tetasy.2005.03.004

  日期：2005.5

  The shortest route at present for the asymmetric synthesis of 3,4-diepipolyoxamic acid 2 and the isomer of polyoxamic acid 5 has been developed via the diastereoselective aldol reaction of carnphor-based tricyclic iminolactones 3 and 4 with good stereoselectivities (dr: 12:1 and 9:1) and high yields. (C) 2005 Elsevier Ltd. All rights reserved.
• New approach to (−)-polyoxamic acid and 3,4-diepipolyoxamic acid from d-lyxono-1,4-lactone
  作者：Céline Falentin、Daniel Beaupère、Gilles Demailly、Imane Stasik

  DOI：10.1016/j.tet.2008.07.095

  日期：2008.10

  The non-natural enantiomer of polyoxamic acid (1) and 3,4-diepipolyoxamic acid (2) was synthesized in four steps from D-lyxono-1,4-lactone (4). Regioselective bromination of unprotected D-lyxono-1,4-lactone with HBr/AcOH led to 2-bromo-2-deoxy-D-xylono-1,4-lactone (5). This intermediate was treated with NaN3 to give 2-azido-2-deoxy-D-lyxono and xylono-1,4-lactones. Saponification of the obtained 2-azido derivatives gave the corresponding 2-azido-2-deoxyaldonic acids salt which, after neutralization followed by reduction, led to the expected compounds: (-)-polyoxamic acid (3) and 3,4-diepipolyoxamic acid (2) in 38% and 29% overall yields. (C) 2008 Elsevier Ltd. All rights reserved.