1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside | 6638-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside
• 英文别名: Methyl-2,3,4-tri-O-benzoyl-β-D-xylopyranosid；Me α-D-Xyl tri-O-benzoate；methyl-(tri-O-benzoyl-β-D-xylopyranoside)；Methyl-(tri-O-benzoyl-β-D-xylopyranosid)；(2R,3R,4S,5R)-2-Methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate；[(3R,4S,5R,6R)-4,5-dibenzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 6638-76-2
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: BMICZGNBUCUNFZ-QSGNWFJVSA-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：

  2,3,4-tri-O-benzoyl-α-D-xylopyranosyl bromide 在 甲醇 作用下， 生成 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside
  参考文献：
  名称：

  The Reaction of Tribenzoyl-β-D-arabinopyranosyl Bromide and Tribenzoyl-α-D-xylopyranosyl Bromide with Methanol

  摘要：

  DOI：

  10.1021/ja01165a093

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。
• On the Role of Neighboring Group Participation and Ortho Esters in β-Xylosylation:  ¹³C NMR Observation of a Bridging 2-Phenyl-1,3-dioxalenium Ion
  作者：David Crich、Zongmin Dai、Stéphane Gastaldi

  DOI：10.1021/jo990424f

  日期：1999.7.1

  The role of ortho esters in the formation of 2,3,4-tri-O-benzoyl-β-xylopyranosides from various donor/promoter pairs has been investigated. It is concluded that for the activation of sulfoxides with Tf2O, thioglycosides with PhSOTf, and bromides with AgOTf the anomeric configuration of the donor is of no consequence on the outcome of the reaction. In all methods studied, the presence or absence of

  已经研究了原酸酯在从各种供体/启动子对形成 2,3,4-三-O-苯甲酰基-β-吡喃木糖苷中的作用。结论是，对于用 Tf2O 活化亚砜，用 PhSOTf 活化硫糖苷，用 AgOTf 活化溴化物，供体的异头构型对反应结果没有影响。在所有研究的方法中，非亲核受阻碱的存在与否至关重要，原酸酯只有在其存在时才能辨别。S-Phenyl 2,3,4-tri-O-benzoyl-1-deoxy-1-thia-β-d-xylopyranoside 合成在三个羰基碳的每一个上都富含 13C。在 CD2Cl2 中，在 -78 °C 下，无论是否有碱许可，用 PhSOTf 激活这种硫糖苷，这是第一次，通过 13C NMR 光谱观察桥接二氧戊环离子作为相邻基团定向糖基化中的中间体。在碱存在的情况下猝灭该阳离子产生原酸酯，而在没有碱的情况下，糖苷是唯一检测到的产物。
• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.
• Selective benzoylation of methyl α- and β-d-xylopyranoside
  作者：Yôtaro Kondo

  DOI：10.1016/s0008-6215(00)80551-0

  日期：1982.9
• The Reaction of Tribenzoyl-β-D-arabinopyranosyl Bromide and Tribenzoyl-α-D-xylopyranosyl Bromide with Methanol
  作者：Hewitt G. Fletcher、C. S. Hudson

  DOI：10.1021/ja01165a093

  日期：1950.9