2-amino-2-deoxy-D-lyxonic acid | 117771-12-7

• 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: 2-amino-2-deoxy-D-lyxonic acid
• 英文别名: (2S,3R,4R)-3,4,5-trihydroxy-2-amino pentanoic acid；3,4-diepipolyoxamic acid；(2S,3R,4R)-2-amino-3,4,5-trihydroxypentanoic acid
• CAS: 117771-12-7
• 化学式: C₅H₁₁NO₅
• 分子量: 165.146
• InChiKey: LYCRDZDACLCUCZ-UZBSEBFBSA-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

• 作为产物：
  描述：

  2-azido-2-deoxy-D-lyxono-1,4-lactone 在 palladium on activated charcoal 盐酸 、 ion-exchange resin Amberlite IR 120 H⁺ 、 氢气 作用下， 以 水 为溶剂， 反应 8.0h， 生成 2-amino-2-deoxy-D-lyxonic acid
  参考文献：
  名称：

  Bols, Mikael; Lundt, Inge, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 67 - 74

  摘要：

  DOI：

文献信息

• An efficient synthesis of polyoxamic acid utilizing the aryl group as the carboxyl synthon. A new approach to polyhydroxyamino acids
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4039(00)75803-5

  日期：——

  Polyoxamic acid (1), an amino acid moiety of antifungal antibiotics polyoxins, has been efficiently synthesized from Boc-(R)4-hydroxyphenylglycine (3) utilizing its aryl group as the carboxyl synthon.
• 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.
• BOLS, MIKAEL;LUNDT, INGE, ACTA CHEM. SCAND., 42,(1988) N 2, 67-74
  作者：BOLS, MIKAEL、LUNDT, INGE

  DOI：——

  日期：——
• 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：——