methyl 2,3,4-tri-O-benzoyl-α-L-arabinopyranoside | 202401-18-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-α-L-arabinopyranoside
• 英文别名: methyl tri-O-benzoyl-α-L-arabinopyranoside；methyl-(tri-O-benzoyl-α-L-arabinopyranoside)；Methyl-(tri-O-benzoyl-α-L-arabinopyranosid)；[(3S,4S,5R,6R)-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 202401-18-1
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: BMICZGNBUCUNFZ-OJXRJRMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 氢溴酸 、 溶剂黄146 作用下， 生成 methyl 2,3,4-tri-O-benzoyl-α-L-arabinopyranoside
  参考文献：
  名称：

  外消旋阿拉伯糖为β-D，L-阿拉伯吡喃糖的证据。

  摘要：

  DOI：

  10.1021/ja01197a046

文献信息

• Sugar migration induced by the Wagner-Meerwein rearrangement of 28- O -glycosyl-betulin derivatives
  作者：Anna Korda、Zbigniew Pakulski、Piotr Cmoch、Katarzyna Gwardiak、Romuald Karczewski

  DOI：10.1016/j.tet.2017.02.024

  日期：2017.3

  3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety

  用TMSOTf处理其中的糖部分连接在28位上的贝特林型皂苷，得到3-O-取代的别贝卢素皂苷。白蛋白核心的Wagner-Meerwein重排驱动了糖部分的这种前所未有的迁移。根据我们的机理研究，在重排过程中释放的氧碳鎓离子与三萜的游离3-OH基团反应，提供了最终的大蒜素皂苷。迁移速率取决于糖部分的大小和构型。
• Antiplasmodial Metabolites Isolated from the Marine Octocoral <i>Muricea austera</i>
  作者：Marcelino Gutiérrez、Todd L. Capson、Héctor M. Guzmán、José González、Eduardo Ortega-Barría、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1021/np060007f

  日期：2006.10.1

  Bioassay-guided fractionation of the MeOH extract from the octocoral Muricea austera collected in the Pacific coast of Panama led to the isolation of eight compounds, including three tyramine derivatives (1-3), two steroidal pregnane glycosides ( 4, 5), and three sesquiterpenoids (6-8). Compounds 2-5 are new natural products, and their structures were determined on the basis of their spectroscopic data (HRMS, 1D and 2D NMR, and CD studies). The antiprotozoal activities of the natural compounds 1-8 as well as those of a series of synthetic glycosides (11-22) and tyramine derivatives (23-35) were evaluated in vitro against a drug-resistant Plasmodium falciparum and intracellular form of Trypanosoma cruzi.
• Ring Closure Studies in the Sugar Benzoates
  作者：M. L. Wolfrom、Clarence C. Christman

  DOI：10.1021/ja01292a010

  日期：1936.1