O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose | 20702-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose
• 英文别名: 1,4-β-cellotetraose；β-cellotetraose；cellotetraose；cellotetrose；β-D-Cellutetraose；Beta-D-Glucopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Glucopyranose；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 20702-56-1
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: LUEWUZLMQUOBSB-HGDSAIHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 水 为溶剂， 反应 0.25h， 以94%的产率得到cellotetrosan
  参考文献：
  名称：

  Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

  摘要：

  Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of mono-saccharides, linear-oligosaccharides, and branched-oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.171
• 作为产物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal sodium methylate 、 氰化汞 、 potassium iodide 作用下， 以 溶剂黄146 为溶剂， 25.0~65.0 ℃ 、101.33 kPa 条件下， 反应 92.0h， 生成 O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose
  参考文献：
  名称：

  纤维二糖，纤维三糖，纤维四糖和乳糖的合成

  摘要：

  摘要1,3,4,6-四-O-乙酰基-α-d-吡喃葡萄糖基溴化物（1）与1,2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷（6）的缩合反应在氰化汞存在下，用1：1的苯-硝基甲烷进行O-脱乙酰化，然后进行柱色谱纯化，产率为86％，将苄基2,3,6-三-O-苄基-β-纤维二糖苷催化水解生成纤维二糖。以类似的方式，使用甲基2,3,6，通过偶联反应以高立体特异性和高收率合成了甲基α-纤维二糖苷，纤维三糖，甲基α-和β-纤维糖苷，纤维四糖，乳糖和甲基α-乳糖苷。 -三-O-苄基-α-和-β-d-吡喃葡萄糖苷6和苄基2,3,6,2'，3'，6'-六-O-苄基-β-纤维二糖苷作为糖基受体，和1,2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物，

  DOI：

  10.1016/0008-6215(83)84014-2

文献信息

• Mass Spectrometric Studies of Fast Pyrolysis of Cellulose
  作者：John C. Degenstein、Matt Hurt、Priya Murria、McKay Easton、Harshavardhan Choudhari、Linan Yang、James Riedeman、Mark S. Carlsen、John J. Nash、Rakesh Agrawal、W. Nicholas Delgass、Fabio H. Ribeiro、Hilkka I. Kenttämaa

  DOI：10.1255/ejms.1335

  日期：2015.6

  A fast pyrolysis probe/linear quadrupole ion trap mass spectrometer combination was used to study the primary fast pyrolysis products (those that first leave the hot pyrolysis surface) of cellulose, cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose, as well as of cellobiosan, cellotriosan, and cellopentosan, at 600°C. Similar products with different branching ratios were found

  使用快速热解探针/线性四极杆离子阱质谱仪组合来研究纤维素、纤维二糖、纤维三糖、纤维四糖、纤维五糖和纤维六糖以及纤维二糖的主要快速热解产物（那些首先离开热解表面的产物） 、纤维三聚糖和纤维戊聚糖，在 600°C。如前所述，在低聚糖和纤维素中发现了具有不同支化率的类似产品。然而，对于纤维三聚糖（和纤维戊聚糖）和纤维素，测量了具有相似支化率的相同产品（除了两个）。该结果表明，纤维三聚糖是研究纤维素快速热解的极好小分子替代物，并且纤维素的大多数快速热解产物并非来自还原端。
• Hydrolysis behaviors of sugarcane bagasse pith in subcritical carbon dioxide–water
  作者：Jiezhen Liang、Xiaopeng Chen、Linlin Wang、Xiaojie Wei、Feifei Qiu、Chaochao Lu

  DOI：10.1039/c6ra18436g

  日期：——

  temperatures (160 to 260 °C), liquid to solid ratios (20 : 1 to 100 : 1), CO2 pressures (0 to 7.3 MPa), stirring speeds (0 to 500 rpm) and reaction times (0 to 40 min). The highest total reducing sugar yield (43.6%) was obtained at 200 °C, liquid to solid ratio 30 : 1, 2 MPa CO2, 500 rpm and 50 min. Two-dimensional heteronuclear single quantum coherence (2D HSQC) nuclear magnetic resonance (NMR), scanning electron

  这项研究的目的是描述蔗糖甘蔗渣髓（SCBP）在亚临界CO 2水中的水解行为。在间歇反应器中使用不同的温度（160至260°C），液固比（20：1至100：1），CO 2压力（0至7.3 MPa），搅拌速度（0至500）进行水解rpm）和反应时间（0到40分钟）。在200°C，液固比30：1、2 MPa CO 2下获得最高的总还原糖收率（43.6％），500 rpm和50分钟。使用二维异核单量子相干（2D HSQC）核磁共振（NMR），扫描电子显微镜（SEM）和傅里叶变换红外光谱（FT-IR）来帮助阐明原料和残留物的物理和化学特性固体颗粒，其结果与水解过程中半纤维素的去除一致。分析了产品浓度随时间的变化，以通过高效液相色谱（HPLC）了解产品分布并推断反应机理。
• Analysis of mono- and oligosaccharides in ionic liquid containing matrices
  作者：Ronny Wahlström、Stella Rovio、Anna Suurnäkki

  DOI：10.1016/j.carres.2012.11.006

  日期：2013.5

  Ionic liquids (ILs), that is, salts with melting points <100 degrees C, have recently attracted a lot of attention in biomass processing due to their ability to dissolve lignocellulosics. In this work, we studied how two imidazolium-based, hydrophilic, cellulose dissolving ionic liquids 1,3-dimethylimidazolium dimethylphosphate [DMIM]DMP and 1-ethyl-3-methylimidazolium acetate [EMIM]AcO affect the usually employed analytical methods for mono- and oligosaccharides, typical products from hydrolytic treatments of biomass. HPLC methods were severely hampered by the presence of ILs with loss of separation power and severe baseline problems, making their use for saccharide quantification extremely challenging. Problems in DNS photometric assay and chromatography were also encountered at high ionic liquid concentrations and many capillary electrophoresis (CE) methods did not allow an efficient analysis of saccharides in these matrices. In this paper we describe an optimized CE method with pre-column derivatization for the qualitative and quantitative analysis of mono- and oligosaccharides in sample matrices containing moderate (20-40% (v/v)) concentrations of ILs. The IL content and type in the sample matrix was found to affect both peak shape and quantification parameters. Generally, the presence of high IL concentrations (>= 20% (v/v)) had a dampening effect on the detection of the analytes. IL in lower concentrations of <20% (v/v) was, however, found to improve peak shape and/or separation in some cases. The optimized CE method has good sensitivity in moderate concentrations of the ionic liquids used, with limits of detection of 5 mg/L for cellooligomers up to the size of cellotetraose and 5-20 mg/L for cellopentaose and cellohexaose, depending on the matrix. The method was used for analysing the action of a commercial beta-glucosidase in ILs and for analysing saccharides in the IL containing hydrolysates from the hydrolysis of microcrystalline cellulose with Trichoderma reesei endoglucanase Cel5A. According to the results, [DMIM]DMP and [EMIM]AcO] showed clear differences in enzyme inactivation. (C) 2012 Elsevier Ltd. All rights reserved.
• Supercritical water treatment for cello-oligosaccharide production from microcrystalline cellulose
  作者：Lasse K. Tolonen、Minna Juvonen、Klaus Niemelä、Atte Mikkelson、Maija Tenkanen、Herbert Sixta

  DOI：10.1016/j.carres.2014.10.012

  日期：2015.1

  Microcrystalline cellulose was treated in supercritical water at 380 degrees C and at a pressure of 250 bar for 0.2, 0.4, and 0.6 s. The yield of the ambient-water-insoluble precipitate and its average molar mass decreased with an extended treatment time. The highest yield of 42 wt % for DP2-9 cello-oligosaccharides was achieved after the 0.4 s treatment. The reaction products included also 11 wt % ambient-water-insoluble precipitate with a DPw of 16, and 6.1 wt % monomeric sugars, and 37 wt % unidentified degradation products. Oligo- and monosaccharide-derived dehydration and retro-aldol fragmentation products were analyzed via a combination of HPAEC-PAD-MS, ESI-MS/MS, and GC-MS techniques. The total amount of degradation products increased with treatment time, and fragmented (glucosyl(n)-erythrose, glucosyl(n)-glycolaldehyde), and dehydrated (glucosyl(n)-levoglucosan) were identified as the main oligomeric degradation products from the cello-oligosaccharides. (C) 2014 Elsevier Ltd. All rights reserved.
• First synthesis of cellooctaose by a convergent synthetic method
  作者：T Nishimura

  DOI：10.1016/s0008-6215(96)00203-0

  日期：1996.11.20