3-O-benzyl-D-xylopyranose | 80235-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyl-D-xylopyranose
• 英文别名: (3R,4S,5R)-4-phenylmethoxyoxane-2,3,5-triol
• CAS: 80235-68-3；80235-69-4
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: UOVFOIAAYUKXOM-YIBTVLSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-D-xylopyranose 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 ytterbium(III) triflate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside
  参考文献：
  名称：

  自动聚糖装配产生的阿拉伯糖木聚糖寡糖对木聚糖解构酶的活性位点图

  摘要：

  木聚糖降解酶对于半纤维素生物质的解构至关重要，因此水解产物可用于各种工业应用，例如生物燃料的生产。为了确定这些酶的底物特异性，我们通过自动聚糖组装制备了复杂的木聚糖寡糖集合。七个差异保护的构建基块为2取代，3取代和2/3取代的阿拉伯糖醛酸和葡萄糖醛酸木聚糖低聚糖的模块化组装提供了基础。木聚糖主链的延长取决于将C4-芴基甲氧基羰基（Fmoc）保护的木糖结构单元反复添加到接头官能化的树脂中。阿拉伯呋喃糖和葡萄糖醛酸残基已通过在木糖结构单元的C2和C3羟基上使用完全正交的2-（甲基）萘基（Nap）和2-（叠氮基甲基）苯甲酰基（Azmb）保护基团选择性地连接至主链。阿拉伯木聚糖低聚糖是绘制涉及木聚糖解构的糖基水解酶活性位点的极佳工具。在寡糖与糖基水解酶孵育后，通过分析消化产物来确定几种木聚糖酶和阿拉伯呋喃糖苷酶的底物特异性。

  DOI：

  10.1002/chem.201605902
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 溶剂黄146 作用下， 生成 3-O-benzyl-D-xylopyranose
  参考文献：
  名称：

  针对聚卡维诺糖苷A的全合成的研究。二糖成分的对映选择性合成

  摘要：

  Mukaiyama-Nicolaou规程适应单未保护的硫代糖苷与糖基氟化物的偶联能够递送标题毒素中存在的异常二糖。

  DOI：

  10.1016/0040-4039(95)00789-f

文献信息

• Stereodivergent synthesis of right- and left-handed iminoxylitol heterodimers and monomers. Study of their impact on β-glucocerebrosidase activity
  作者：Fabien Stauffert、Jenny Serra-Vinardell、Marta Gómez-Grau、Helen Michelakakis、Irene Mavridou、Daniel Grinberg、Lluïsa Vilageliu、Josefina Casas、Anne Bodlenner、Antonio Delgado、Philippe Compain

  DOI：10.1039/c7ob00443e

  日期：——

  A library of dimers and heterodimers of both enantiomers of 2-O-alkylated iminoxylitol derivatives has been synthesised and evaluated on β-glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (GD). Although the objective was to target simultaneously the active site and a secondary binding site of the glucosidase, the (−)-2-iminoxylitol moiety seemed detrimental for imiglucerase inhibition

  已经合成了2- O-烷基化的亚氨木糖醇衍生物的两个对映异构体的二聚体和异二聚体文库，并在β-葡萄糖脑苷脂酶（GCase）上进行了评估，该酶是引起高雪氏病（GD）的酶。尽管目的是同时靶向葡糖苷酶的活性位点和次级结合位点，但（-）-2-亚氨基羟醇部分似乎对伊美苷酶抑制有害，并且在G202R，N370S和L444P成纤维细胞中未获得明显的增强。但是，所有具有至少一种（+）-2- O-烷基亚氨木糖醇的化合物都是纳摩尔范围内的GCase抑制剂，并且在G202R纤维刀片中是显着的GCase活性增强剂，这已通过糖基神经酰胺水平的降低和共定位研究得到证实。 。
• Studies directed toward the total synthesis of polycavernoside A. Enantioselective synthesis of the disaccharide component
  作者：Jeffrey N. Johnston、Leo A. Paquette

  DOI：10.1016/0040-4039(95)00789-f

  日期：1995.6

  Adaptation of the Mukaiyama-Nicolaou protocol to the coupling of a monounprotected thioglycoside to a glycosyl fluoride is capable of delivering the unusual disaccharide present in the title toxin.

  Mukaiyama-Nicolaou规程适应单未保护的硫代糖苷与糖基氟化物的偶联能够递送标题毒素中存在的异常二糖。
• Automated Synthesis of Arabinoxylan-Oligosaccharides Enables Characterization of Antibodies that Recognize Plant Cell Wall Glycans
  作者：Deborah Schmidt、Frank Schuhmacher、Andreas Geissner、Peter H. Seeberger、Fabian Pfrengle

  DOI：10.1002/chem.201500065

  日期：2015.4.7

  wall glycans are used for high‐resolution imaging, providing important information about the structure and function of cell wall polysaccharides. To characterize the binding epitopes of these powerful molecular probes a library of eleven plant arabinoxylan oligosaccharides was produced by automated solid‐phase synthesis. Modular assembly of oligoarabinoxylans from few building blocks was enabled by adding

  识别植物细胞壁聚糖的单克隆抗体用于高分辨率成像，可提供有关细胞壁多糖结构和功能的重要信息。为了表征这些功能强大的分子探针的结合表位，通过自动固相合成制备了11种植物阿拉伯木聚糖寡糖文库。通过将（2-萘基）甲基（Nap）添加到用于固相合成的正交保护基的工具箱中，可以使来自几个结构单元的低聚阿拉伯木聚糖的模块组装成为可能。获得缀合就绪的寡糖，并在微阵列上确定了木聚糖定向抗体的结合特异性。
• A Structural Study of Di-<i>O</i>-isopropyridene-pentitols by Conversion to the Corresponding Mono-<i>O</i>-benzyl Derivatives
  作者：Toshio Nakagawa、Hisao Tokuoka、Kazuhiko Shinoto、Juji Yoshimura、Tetsuo Sato

  DOI：10.1246/bcsj.40.2150

  日期：1967.9

  d-Arabinitol and xylitol were acetonated, benzylated and then hydrolyzed with a mineral acid to afford in good yields the corresponding 1-O-benzyl derivatives, which were identified by a periodate oxidation and a chemical identification. A preferential acetonation of the pentitols is discussed in a view of stereochemistry. Synthesis of 2-O-benzyl-d-arabinitol and 3-O-benzylxylitol are also described.

  d-Arabinitol 和木糖醇被乙腈化、苄基化，然后用矿物酸水解，得到相应的 1-O 苄基衍生物，产量很高。从立体化学的角度讨论了戊醇的优先缩酮作用。此外还介绍了 2-O-苄基-d-阿拉伯糖醇和 3-O-苄基木糖醇的合成。
• Stereocontrolled Elaboration of Natural (−)-Polycavernoside A, a Powerfully Toxic Metabolite of the Red Alga <i>Polycavernosa</i> <i>tsudai</i>
  作者：Leo A. Paquette、Louis Barriault、Dmitri Pissarnitski、Jeffrey N. Johnston

  DOI：10.1021/ja993487o

  日期：2000.2.1

  A stereoselective total synthesis of natural levorotatory polycavemoside A (1) has been achieved. initial investigations produced the properly activated disaccharide unit 18b via the conjoining of building blocks originating from L-fucose and D-xylose. This objective was followed by preparation of the phenylsulfonyl-substituted tetrahydropyran 23 and aldehyde 30. After proper linking of these key compounds, important information had to be garnered on the sequence of steps that would ultimately result in successful access to 1. Although oxidation to generate alpha-diketone 35 and unmasking of the C-13 hydroxyl did give rise efficiently to lactol 36, this functionality did not pave the way for ensuring macrolactonization. When this sequence of steps was reversed, it was indeed possible to arrive at the heavily functionalized precursor 43. However, numerous experiments failed to result in the requisite activation of C-16 for attachment of the trienyl side chain. However, if the E-vinyl iodide was elaborated in advance of alpha-diketone generation, glycosidation, and complete side chain construction, arrival at 1 proceeded without unsurmountable complications to furnish the targeted marine toxin.