2,2'-oxydiethyl bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) | 454424-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-oxydiethyl bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)
• 英文别名: 1,5-bis(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-oxapentane；bis-[2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-ethyl]-ether；Bis-[2-(tetra-O-acetyl-β-D-glucopyranosyloxy)-aethyl]-aether；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[2-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethoxy]ethoxy]oxan-2-yl]methyl acetate
• CAS: 454424-76-1
• 化学式: C₃₂H₄₆O₂₁
• 分子量: 766.705
• InChiKey: GBESCZXEBZQUDZ-HNGBAHPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  257
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2,2'-oxydiethyl bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective complexation of chiral linear hosts containing monosaccharide moieties with chiral organic amines

  摘要：

  New chiral linear hosts (1-3. a: peracetylated derivatives. b: permethylated derivatives) containing monosaccharide end groups were designed on the basis of the structural features of permethylated 1(F)-fructonystose (MeFruNys), which shows a remarkable chiral discrimination ability, and then synthesized. The chiral discrimination ability of their hosts toward chiral organic ammonium guests were evaluated using FAB mass spectrometry and H-1 NMR. Their hosts showed chiral discrimination for some guests. As the contrasting compounds (4 and 5) hardly showed any chiral discrimination, it was clarified that the structural features extracted from MeFruNys are very significant factors for chiral recognition. The H-1 NMR shift induced by adding a potassium ion (counter anion: SCN-) in (CD3)(2)CO suggested that the cation moiety of the chiral guests was located at the binding site consisting of the -O-C-C-O- units and the ring-oxygens of the saccharide moieties. The structure of the complex of host 1b with 1-(1-naphthyl)ethylammonium ion (NEAP) was estimated by the 1H NMR induced shifts and the molecular dynamics simulation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00351-4
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 1,4-二氧六环 、 silver carbonate 作用下， 生成 2,2'-oxydiethyl bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of Glycol Glucosides¹

  摘要：

  DOI：

  10.1021/ja01861a058

文献信息

• Synthesis and characterization of a small library of bisglucosides: Influence of the nature of the diol/diphenol used in O-glucosylation
  作者：Stéphane Patry、Mike Robitzer、Jean-Pierre Habas

  DOI：10.1016/j.carres.2020.108217

  日期：2021.2

  completed by MALDI-TOF MS technique. The nucleophilicity of these dihydroxy compounds is identified as being the main factor that governs the reaction characteristics. In particular, the best selectivity is obtained with the use of hydroquinone. Inversely, by-products (oligomers, deacetylated compounds) are observed with the diols defined by higher nucleophilicity despite the choice of stereoselective

  在本文中，通过两个乙酰化葡萄糖单元与二醇（或二酚）的反应研究了不同双糖苷的合成，以开发一个通用的分子平台，用于未来生物基聚合物的发展。最初使用一组五种二醇和一种二酚，以检查它们的化学骨架对反应产率以及所形成物质的性质和比例的影响。使用由 MALDI-TOF MS 技术完成的 1H 和 13C NMR 光谱鉴定反应产物。这些二羟基化合物的亲核性被认为是控制反应特性的主要因素。特别是，使用对苯二酚可获得最佳选择性。相反，副产品（低聚物、