methyl α-L-arabinofuranosyl-(1->3)-β-D-xylopyranoside | 93130-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-L-arabinofuranosyl-(1->3)-β-D-xylopyranoside
• 英文别名: Methyl 3-O-(α-L-arabinofuranosyl)-β-D-xylopyranoside；methyl-3-O(α-L-arabinofuranosyl)-β-D-xylopiranoside；Methyl 3-O-(α-arabinofuranosyl)-β-D-xylopyranoside；methyl 2-O-α-L-arabinofuranosyl-β-D-xylopyranoside；Araf(a1-3)b-Xyl1Me；(2R,3R,4S,5R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-methoxyoxane-3,5-diol
• CAS: 93130-21-3
• 化学式: C₁₁H₂₀O₉
• 分子量: 296.274
• InChiKey: NBJQIIABXABZFS-QWSSHKGKSA-N

物化性质

• 沸点：
  588.6±50.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl α-L-arabinofuranosyl-(1->3)-β-D-xylopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 24.0h， 生成 methyl (2,3-di-O-acetyl-α-L-arabinofuranosyl)-(1->3)-2,4-di-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  羟基肉桂酸甲基α-L-阿拉伯呋喃糖基-（1-> 2）-和（1-> 3）-β-D-吡喃吡喃糖苷的合成及光谱表征。

  摘要：

  制备甲基5-O-阿魏酰基-α-L-阿拉伯呋喃糖基-（1-> 3）-β-D-吡喃吡喃糖苷，伴随的5-Op-香豆酰二糖及其（1-> 2）已开发类似物。（1-> 3）羟基肉桂酸二糖可从L-阿拉伯糖和甲基β-D-吡喃吡喃糖苷分11步获得，总产率为17％（基于甲基β-D-吡喃吡喃糖苷）。分9个步骤制备了相应的（1-2）材料，总产率> 37％。完整的光谱表征为与从植物细胞壁分离的类似物质进行比较提供了明确的指配。关于耦合常数信息，讨论了所准备材料的构象方面。

  DOI：

  10.1016/0008-6215(93)84168-6
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl chloride 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 methyl α-L-arabinofuranosyl-(1->3)-β-D-xylopyranoside
  参考文献：
  名称：

  羟基肉桂酸甲基α-L-阿拉伯呋喃糖基-（1-> 2）-和（1-> 3）-β-D-吡喃吡喃糖苷的合成及光谱表征。

  摘要：

  制备甲基5-O-阿魏酰基-α-L-阿拉伯呋喃糖基-（1-> 3）-β-D-吡喃吡喃糖苷，伴随的5-Op-香豆酰二糖及其（1-> 2）已开发类似物。（1-> 3）羟基肉桂酸二糖可从L-阿拉伯糖和甲基β-D-吡喃吡喃糖苷分11步获得，总产率为17％（基于甲基β-D-吡喃吡喃糖苷）。分9个步骤制备了相应的（1-2）材料，总产率> 37％。完整的光谱表征为与从植物细胞壁分离的类似物质进行比较提供了明确的指配。关于耦合常数信息，讨论了所准备材料的构象方面。

  DOI：

  10.1016/0008-6215(93)84168-6

文献信息

• Pentoside Synthesis by Dehydrative Glycosylation. Synthesis of<i>O</i>-α-L-Arabinofuranosyl-(1→3)-<i>O</i>-β-D-xylopyranosyl-(1→4)-D-xylopyranose
  作者：Shinkiti Koto、Naohiko Morishima、Kazuhiro Takenaka、Chisa Uchida、Shonosuke Zen

  DOI：10.1246/bcsj.58.1464

  日期：1985.5

  O-α-l-Arabinofuranosyl-(1→3)-O-β-d-xylopyranosyl-(1→4)-d-xylopyranose isolated from the hydrolyzate of corncobs arabinoxylan was synthesized by way of dehydrative glycosylation.

  来自玉米芯阿拉伯木聚糖水解物的O-α-l-阿拉伯呋喃糖基-(1→3)-O-β-d-木吡喃糖基-(1→4)-d-木吡喃糖是通过脱水缩合糖基化合成的。
• New mediators for the enzyme laccase: mechanistic features and selectivity in the oxidation of non-phenolic substrates
  作者：Paola Astolfi、Paolo Brandi、Carlo Galli、Patrizia Gentili、Maria Francesca Gerini、Lucedio Greci、Osvaldo Lanzalunga

  DOI：10.1039/b507657a

  日期：——

  New mediators of laccase have been comparatively evaluated and ranked towards the benchmark aerobic oxidation of p-MeO-benzyl alcohol. The mechanism of oxidation of this non-phenolic substrate by each mediator, which is initially oxidised by laccase to the Medox form, has been assessed among three alternatives. The latter make the phenoloxidise laccase competent for the indirect oxidation of non-phenolic (and thus ‘unnatural’) substrates. Experimental characterisation of the mediators, by means of spectrophotometric, electrochemical and thermochemical survey, is reported. Clear-cut evidence for the formation of a benzyl radical intermediate in the oxidation of a particular benzyl alcohol with laccase and a N–OH mediator is attained by means of a trapping experiment. The selectivity of the laccase-catalysed oxidation of two competing lignin and polysaccharide model compounds has been assessed by using the highly proficient 4-MeO-HPI mediator, and found very high in favour of the former model. This evidence is in keeping with the operation of a radical hydrogen-abstraction process that efficiently cleaves the benzylic rather than the aliphatic C–H bond of the two models. Significant is the finding that catechol, i.e., a model of recurring phenolic structures in lignin, once oxidised to aryloxyl radical by laccase is capable to mediate a radical oxidation of non-phenolic compounds. This supports a fully-fledged role of laccase as a delignifying enzyme in nature by way of no other mediators than the very phenolic groups of lignin. Finally, an evaluation of the dissociation energy of the NO–H bond of HBT, which is not accessible experimentally, is provided by the use of a thermochemical cycle and theoretical calculations.

  针对对-MeO-苄醇的有氧氧化基准，对漆酶的新介质进行了比较评估和排序。每种介质氧化这种非酚类底物的机理都在三种备选方案中进行了评估。后者使酚氧化漆酶能够间接氧化非酚（因此是 "非天然 "的）底物。报告通过分光光度法、电化学法和热化学法对介质进行了实验表征。通过诱捕实验，清楚地证明了在漆酶和 N-OH 介质氧化特定苄醇的过程中形成了苄基自由基中间体。通过使用高度熟练的 4-MeO-HPI 媒介剂，对漆酶催化氧化两种相互竞争的木质素和多糖模型化合物的选择性进行了评估，结果发现前一种模型的选择性非常高。这一证据与自由基氢萃取过程的操作相吻合，该过程能有效地裂解两种模型中的苄基而非脂肪族 C-H 键。重要的是，儿茶酚（即木质素中重复出现的酚类结构模型）一旦被漆酶氧化成芳基自由基，就能介导非酚类化合物的自由基氧化。这支持了漆酶作为脱木质素酶在自然界中的全面作用，除了木质素中的酚基外，没有其他媒介。最后，利用热化学循环和理论计算，对 HBT 的 NO-H 键的解离能进行了评估。
• Toikka, Merja; Brunow, Gosta, Journal of the Chemical Society. Perkin transactions I, 1999, # 13, p. 1877 - 1883
  作者：Toikka, Merja、Brunow, Gosta

  DOI：——

  日期：——
• Synthesis and spectroscopic characterization of hydroxycinnamoylated methyl α-l-arabinofuranosyl-(1 → 2)- and (1 → 3)-β-d-xylopyranosides
  作者：Richard F. Helm、John Ralph

  DOI：10.1016/0008-6215(93)84168-6

  日期：1993.2

  preparation of methyl 5-O-feruloyl-alpha-L- arabinofuranosyl-(1-->3)-beta-D-xylopyranoside, the companion 5-O-p-coumaroyl disaccharide, and their (1-->2) analogs has been developed. The (1-->3) hydroxycinnamoylated disaccharides are available in 11 steps from L-arabinose and methyl beta-D-xylopyranoside in 17% overall yield (based on methyl beta-D-xylopyranoside). The corresponding (1-->2) materials were

  制备甲基5-O-阿魏酰基-α-L-阿拉伯呋喃糖基-（1-> 3）-β-D-吡喃吡喃糖苷，伴随的5-Op-香豆酰二糖及其（1-> 2）已开发类似物。（1-> 3）羟基肉桂酸二糖可从L-阿拉伯糖和甲基β-D-吡喃吡喃糖苷分11步获得，总产率为17％（基于甲基β-D-吡喃吡喃糖苷）。分9个步骤制备了相应的（1-2）材料，总产率> 37％。完整的光谱表征为与从植物细胞壁分离的类似物质进行比较提供了明确的指配。关于耦合常数信息，讨论了所准备材料的构象方面。