1,4-anhydro-2,3,5,6-tetra-O-(p-methoxybenzyl)-4-seleno-D-galactitol | 784151-30-0

• 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: 1,4-anhydro-2,3,5,6-tetra-O-(p-methoxybenzyl)-4-seleno-D-galactitol
• CAS: 784151-30-0
• 化学式: C₃₈H₄₄O₈Se
• 分子量: 707.723
• InChiKey: ABZHACJIFUALAS-UYFSSDKWSA-N

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2,3,5,6-tetra-O-(p-methoxybenzyl)-4-seleno-D-galactitol 在 三氟乙酸 作用下， 反应 1.0h， 生成 (2S,3R,4R)-2-((R)-1,2-Dihydroxy-ethyl)-tetrahydro-selenophene-3,4-diol
  参考文献：
  名称：

  碳水化合物基硒醚和硫醚的温和类推子反应，涉及线性乙酸酯作为推定的中间体

  摘要：

  研究了含硒和硫的基于碳水化合物的杂环的类 Pummerer 重排。据我们所知，这是关于硒杂环中Pummerer 重排的第一份报告。含硫或硒作为环杂原子的 1,4-脱水-D-半乳糖醇或 1,5-anhydroxylitol 衍生物的臭氧化产生归因于臭氧化物的不稳定中间体。这些中间体在加热时分解，得到硒氧化物或亚砜。值得注意的是，在低温下向臭氧化反应混合物中加入乙酸酐，在升温至环境温度后得到普默勒重排产物。然而，当分离出的硒氧化物或亚砜用乙酸酐处理时，会发生普默勒重排，但亚砜需要更高的反应温度。后一个结果与前一个结果不同，并根据前一种情况下的臭氧乙酸中间体的重排来解释。为了探究重排是通过单线态氧的挤出进行异裂还是通过自由基的产生进行均裂，进行了红荧烯的捕获实验和自由基陷阱 DMPO 的电子顺磁共振 (EPR) 研究。这些实验的结果与自由基物种的中间性一致，并提出了一种新的、更温和的合成方法来生成

  DOI：

  10.1021/ja0557029
• 作为产物：
  描述：

  (3R,4S,5R)-5-[(R)-1,2-Bis-(4-methoxy-benzyloxy)-ethyl]-3,4-bis-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ol 在 吡啶 、 sodium selenide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 1,4-anhydro-2,3,5,6-tetra-O-(p-methoxybenzyl)-4-seleno-D-galactitol
  参考文献：
  名称：

  Synthesis of novel ammonium and selenonium ions and their evaluation as inhibitors of UDP-galactopyranose mutase

  摘要：

  The syntheses of two ammonium salts of 1,4-dideoxy-1,4-imino-D-galactitol containing erythritol sulfate side chains are described. The parent compound is a known inhibitor of the enzyme UDP-galactopyranose mutase (UDP-galactopyranose furanomutase, E.C. 5.4.99.9), which is responsible for the conversion of UDP-galactopyranose into UDP-galactofuranose and is presumably protonated in its active form. The side chain was chosen because it is present in a known sulfonium ion alpha-glucosidase inhibitor, salacinol. The syntheses of the selenonium analogues derived from 1,4-dideoxy-1,4-seleno-D-galactitol are also described. The synthetic strategy in the syntheses of all four salts involved the nucleophilic attack of a protected derivative of the alditol at the least hindered carbon of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate to give adducts that were subsequently deprotected. The importance of different protecting groups used in the various syntheses is also highlighted. Enzyme inhibition assays carried out on these compounds, and the corresponding sulfonium ions synthesized previously, show that they are poor inhibitors of UDP-galactopyranose mutase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.012