methyl-2',3',4'-tri-O-benzoyl-β-L-arabinopyranoside | 10225-76-0

• 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-β-L-arabinopyranoside
• 英文别名: Methyl-2,3,4-tri-O-benzoyl-β-L-lyxo-pyranosid；[(3S,4S,5R,6S)-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 10225-76-0
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: BMICZGNBUCUNFZ-TZKYFUQOSA-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：

  methyl L-arabinoside 、 苯甲酰氯 在 吡啶 作用下， 以185 mg的产率得到methyl-2',3',4'-tri-O-benzoyl-β-L-arabinopyranoside
  参考文献：
  名称：

  Antiplasmodial Metabolites Isolated from the Marine Octocoral Muricea austera

  摘要：

  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.

  DOI：

  10.1021/np060007f

文献信息

• Utilization of Sugars in Organic Synthesis. XXIII. Part XXII: Lithium Aluminum Hydride Reduction of Glycopyranoside-Monosulfonates: Formation of Branched Furanosides.
  作者：Yoshisuke TSUDA、Makoto NISHIMURA、Yoko ITO

  DOI：10.1248/cpb.39.1983

  日期：——

  Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions : (1) stereospecific 1, 2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O : for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.

  乙醇醛糖苷-单甲磺酸酯的锂铝氢还原引发了三种反应：(1) 立体特异性的1,2-移位，生成分支呋喃糖苷(路径A)，(2) 还原性O-S键断裂，生成原始糖苷(路径B)，以及(3) 甲磺酰氧基的还原性移除，生成去氧糖苷(路径C)。在2-O、3-O和4-O位置的单甲磺酸酯中，路径A反应尤为显著；例如，甲基2-O-甲磺酰-α-D-木糖吡喃糖苷以60%的产率转化为甲基2-脱氧-2-C-(羟甲基)-α-D-赤藓呋喃糖苷。该反应为天然与非天然型分支糖呋喃糖苷的合成开辟了一条新颖高效的途径。本反应的立体电子学需求与其余两种反应的平衡关系在此讨论。