Methyl 2,3-di-O-benzyl-β-D-xylopyranoside | 80973-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,3-di-O-benzyl-β-D-xylopyranoside
• 英文别名: 1-O-methyl-2,3-di-O-benzyl-β-D-xylopyranose
• CAS: 80973-59-7
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: MPJMCGOAPDMRLO-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,3-di-O-benzyl-β-D-xylopyranoside 在 palladium on activated charcoal 吡啶 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 methyl 4-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of new methyl O-acetyl-α- and -β-d-xylopyranosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)80804-6
• 作为产物：
  描述：

  甲基 2,3-脱水-beta-D-核吡喃糖苷 在 palladium on activated charcoal 氢氧化钾 、 sodium hydride 作用下， 以 丙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 Methyl 2,3-di-O-benzyl-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of new methyl O-acetyl-α- and -β-d-xylopyranosides

  摘要：

  DOI：

  10.1016/s0008-6215(00)80804-6

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。
• Synthesis and structural studies of “branched” 2‐linked trisaccharides related to h‐type 2 blood group determinants
  作者：Jens Ø. Duus、Nikolay E. Nifant'ev、Alexander S. Shashkov、Elena A. Khatuntseva、Klaus Bock

  DOI：10.1560/lxum-gkyp-r6rf-08tf

  日期：2000.12

  A series of fucosylated trisaccharides l-Fuc-(12)-ß-d-Gal-(14)-ß-X-OMe (1-6, X = d-GlcNAc, d-Qui (6-deoxy-Glc), d-Xyl) related to H type 2 blood group determinant have been synthesized both as their α- and ß- L-Fuc anomers together with the component disaccharide starting compounds (7-11). The conformational properties of the trisaccharides together with their parent disaccharides have been investigated

  一系列岩藻糖基化的三糖l-Fuc-（12）-ß-d-Gal-（14）-ß-X-OMe（1-6，X = d-GlcNAc，d-Qui（6-deoxy-Glc），已经合成了与H 2型血型决定因素有关的d-Xyl），它们分别是α-和ß-L-Fuc异构体以及二糖类起始化合物（7-11）。三糖及其母体二糖的构象性质已通过NMR光谱法（质子和碳化学位移以及质子NOE）结合蒙特卡罗方法和HSEA力场的计算机建模（使用GEGOP程序）进行了研究在α-连接的岩藻糖系列上。
• Design, synthesis, FGF-1 binding, and molecular modeling studies of conformationally flexible heparin mimetic disaccharides
  作者：Ligong Liu、Ian Bytheway、Tomislav Karoli、Jon K. Fairweather、Siska Cochran、Caiping Li、Vito Ferro

  DOI：10.1016/j.bmcl.2007.10.071

  日期：2008.1

  Disaccharide mimetics of a heparin sequence that binds to fibroblast growth factors were prepared by coupling a D-galactose donor with a methyl beta-D-gluco- or xylopyranoside acceptor. When fully sulfated, the glucose or xylose moieties exist in solution in equilibrium between the (4)C1 and (1)C4 conformers, as confirmed by 1H NMR spectroscopy, thus mimicking the conformationally flexible L-iduronic

  通过将D-半乳糖供体与甲基β-D-葡萄糖-或吡喃吡喃糖苷受体偶联来制备与成纤维细胞生长因子结合的肝素序列的二糖模拟物。当完全硫酸化后，葡萄糖或木糖部分以平衡状态存在于（4）C1和（1）C4构象异构体之间的溶液中，这已通过1H NMR光谱学证实，从而模仿了肝素中的构象柔性L-艾杜糖醛酸。对接计算显示，FGF-1结合位点中二糖磺基的预测位置与肝素衍生的共结晶寡糖所观察到的位置一致。预测的结合亲和力与从结合测定获得的实验Kd值一致，并且与模型肝素二糖的预测值相似。
• Acetyl Group Migration in Xylan and Glucan Model Compounds as Studied by Experimental and Computational Methods
  作者：Robert Lassfolk、Manuel Pedrón、Tomás Tejero、Pedro Merino、Johan Wärnå、Reko Leino

  DOI：10.1021/acs.joc.2c01956

  日期：2022.11.4

  saccharide unit but also between two different saccharide units. Kinetics of this phenomenon were previously investigated in both mannan model compounds and a naturally occurring polysaccharide. In addition to mannans, there are also several other naturally acetylated polysaccharides, such as xyloglucans and xylans. Both xyloglucans and xylans are some of the most common acetylated polysaccharides in nature

  我们最近证明，低聚糖中的乙酰基不仅可以在一个糖单元内迁移，而且可以在两个不同的糖单元之间迁移。这种现象的动力学以前在甘露聚糖模型化合物和天然存在的多糖中进行过研究。除甘露聚糖外，还有其他几种天然乙酰化多糖，例如木葡聚糖和木聚糖。木葡聚糖和木聚糖都是自然界中最常见的乙酰化多糖，在植物细胞中发挥着重要作用。考虑到天然多糖的各种生物学作用，可以假设乙酰基的分子内迁移也可能与自然界中多糖的生物活性调节有关。最后，更好地了解糖苷键的整体迁移现象可能有助于了解此类迁移在多糖生物活性背景下的潜在作用。在这里，我们通过实验和计算方法的结合，对合成的木聚糖和葡聚糖三糖模型化合物中的乙酰基迁移进行了详细研究，表明糖单元之间的迁移从一个糖单元的仲羟基向一级羟基转移另一个单元的羟基。
• Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors
  作者：Andrew B. Mayfield、Jan B. Metternich、Adam H. Trotta、Eric N. Jacobsen

  DOI：10.1021/jacs.0c00335

  日期：2020.2.26

  We report a new method for stereoselective O-furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2-cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.