2'(E),7'-octadienyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside | 677027-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'(E),7'-octadienyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside
• 英文别名: [(3S,4S,5R,6R)-4,5-diacetyloxy-6-[(2E)-octa-2,7-dienoxy]oxan-3-yl] acetate
• CAS: 677027-92-8
• 化学式: C₁₉H₂₈O₈
• 分子量: 384.427
• InChiKey: HWXYYGKPNDJRBC-BNHLBDIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'(E),7'-octadienyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以97%的产率得到2-(E)-7-octadienyl α-L-arabinopyranoside
  参考文献：
  名称：

  Neutral pentosides surfactants issued from the butadiene telomerization with pentoses: preparation and amphiphilic properties

  摘要：

  Interfacial properties of octadienyl pentosides prepared by the palladium-catalyzed telomerization of butadiene with free pentoses have been evaluated and compared to those of mixtures issued from the autoclaving process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.023
• 作为产物：
  描述：

  L-阿拉伯糖 、 乙酸酐 、 1,3-丁二烯 在 tris(dibenzylideneacetone)dipalladium (0) sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以11%的产率得到2'(E),7'-octadienyl 2,3,4-tri-O-acetyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Neutral pentosides surfactants issued from the butadiene telomerization with pentoses: preparation and amphiphilic properties

  摘要：

  Interfacial properties of octadienyl pentosides prepared by the palladium-catalyzed telomerization of butadiene with free pentoses have been evaluated and compared to those of mixtures issued from the autoclaving process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.023

文献信息

• Telomerization of Butadiene withL-Arabinose andD-Xylose in DMF: Selective Formation of their Monooctadienyl Glycosides
  作者：Boris Estrine、Sandrine Bouquillon、Françoise Hénin、Jacques Muzart

  DOI：10.1002/ejoc.200400064

  日期：2004.7

  Conditions to achieve the palladium-catalysed telomerization of butadiene with L-arabinose and D-xylose as telogens have been identified. With DMF as solvent, optimised ratios of substrate, reactants and catalytic system allowed the selective grafting of one octadienyl chain onto the anomeric hydroxy group. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  已经确定了用 L-阿拉伯糖和 D-木糖作为调聚剂实现钯催化的丁二烯调聚的条件。以 DMF 作为溶剂，优化的底物、反应物和催化体系的比例允许一个辛二烯链选择性接枝到异头羟基上。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Palladium-Catalyzed Telomerization of Butadiene with Tri-O-acetylated Pentoses as a Convenient Route to 2,7-Octadienyl Glycosides
  作者：Françoise Hénin、Alla Bessmertnykh、Anna Serra-Muns、Jacques Muzart、Henri Baillia

  DOI：10.1002/ejoc.200300606

  日期：2004.2

  Palladium-catalyzed telomerization of butadiene with O-acetylated pyranoses having a free anomeric hydroxyl group was applied for synthesis of octadienyl glycosides. The ratio of linear to branched glycosides depends dramatically on the conditions used. By careful optimization of reaction parameters the highly selective formation (95:5) of linear glycosides was achieved. An extended mechanism of the

  钯催化丁二烯与具有游离异头羟基的 O-乙酰化吡喃糖的调聚反应用于合成辛二烯糖苷。直链与支链糖苷的比例很大程度上取决于所用的条件。通过仔细优化反应参数，实现了线性糖苷的高选择性形成 (95:5)。提出了调聚反应的扩展机制。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)