sodium lactobionate | 27297-39-8

• 物质功能分类: 有机原料 - 有机金属盐
• 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: sodium lactobionate
• 英文别名: sodium;(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 27297-39-8
• 化学式: C₁₂H₂₁O₁₂*Na
• 分子量: 380.281
• InChiKey: AQKFVNLHZYOMKQ-WWNCWODVSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -10.0
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  220
• 氢给体数：
  8
• 氢受体数：
  12

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  RT

制备方法与用途

用途：用于合成乳糖酸红霉素的中间体。

反应信息

• 作为产物：
  描述：

  乳糖 在 bismuth(III) nitrate 、 palladium on activated charcoal sodium hydroxide 、 水 、 氧气 作用下， 49.9 ℃ 、100.0 kPa 条件下， 生成 sodium lactobionate
  参考文献：
  名称：

  The effect of bismuth on the selective oxidation of lactose on supported palladium catalysts

  摘要：

  The selective oxidation of lactose by molecular oxygen has been studied in a batch reactor containing an aqueous slurry of 0.5 kmol m-1 reactant and 1.0 kg m-3 catalyst. The in situ Bi promotion of a commercial Pd-C catalyst resulted in 100% selectivity to sodium lactobionate up to conversions of 95% in the pH range 7-10 and at temperatures up to 333 K. Performing the reaction under such conditions that the oxygen transfer to the liquid phase was rate-controlling allowed the production of sodium lactobionate in high yields in approximately 1 h. A maximum initial reaction-rate of 0.47 mol kg-1 s-1 was found at a molar Bi to Pd ratio of 0.50-0.67. Fifteen batches of lactose were oxidized with the same charge of catalyst without significant loss in initial activity or selectivity. Such other aldoses as maltose, glucose, and galactose could be oxidized analogously with similar selectivities.

  DOI：

  10.1016/0008-6215(90)84027-r

文献信息

• Gold Catalysis and Photoactivation: A Fast and Selective Procedure for the Oxidation of Free Sugars
  作者：Mehdi Omri、Frédéric Sauvage、Yan Busby、Matthieu Becuwe、Gwladys Pourceau、Anne Wadouachi

  DOI：10.1021/acscatal.7b03394

  日期：2018.3.2

  A fast and efficient methodology for the selective oxidation of sugars into corresponding sodium aldonates is herein reported. Hydrogen peroxide was used as a cheap oxidant and electron scavenger, in the presence of only 0.003–0.006 mol % of gold in basic conditions. Three photocatalysts were studied, namely Au/Al2O3, Au/TiO2, and Au/CeO2, the latter being the most efficient (TOF > 750 000 h–1) and

  本文报道了一种快速有效的方法，用于将糖选择性氧化为相应的醛酸钠。过氧化氢被用作廉价的氧化剂和电子清除剂，在碱性条件下仅存在0.003-0.006 mol％的金。研究了三种光催化剂，即Au / Al 2 O 3，Au / TiO 2和Au / CeO 2，后者是最有效的（TOF> 750 000 h –1）且具有完美的选择性。在标准入射阳光照射（AM1.5G条件下，100 mW / cm 2）下仅暴露10分钟）可将葡萄糖完全转化为相应的葡萄糖酸钠。证明了其多功能性，该方法已成功地应用于各种寡糖，无需任何纯化步骤即可定量获得产量和高纯度（> 95％）的相应醛酸。通过简单的过滤回收光催化剂，并重复使用5次，照射10分钟后可获得相同的转化率和选择性。
• The effect of bismuth on the selective oxidation of lactose on supported palladium catalysts
  作者：Henricus E.J. Hendriks、Ben F.M. Kuster、Guy B. Marin

  DOI：10.1016/0008-6215(90)84027-r

  日期：1990.9

  The selective oxidation of lactose by molecular oxygen has been studied in a batch reactor containing an aqueous slurry of 0.5 kmol m-1 reactant and 1.0 kg m-3 catalyst. The in situ Bi promotion of a commercial Pd-C catalyst resulted in 100% selectivity to sodium lactobionate up to conversions of 95% in the pH range 7-10 and at temperatures up to 333 K. Performing the reaction under such conditions that the oxygen transfer to the liquid phase was rate-controlling allowed the production of sodium lactobionate in high yields in approximately 1 h. A maximum initial reaction-rate of 0.47 mol kg-1 s-1 was found at a molar Bi to Pd ratio of 0.50-0.67. Fifteen batches of lactose were oxidized with the same charge of catalyst without significant loss in initial activity or selectivity. Such other aldoses as maltose, glucose, and galactose could be oxidized analogously with similar selectivities.