甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 | 7216-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷
• 中文别名: 甲基4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷
• 英文名称: methyl β-D-cellobioside
• 英文别名: methyl β-cellobioside；Methyl-β-cellobiosid；methyl cellobioside；Methyl-β-D-cellobiosid；β-Methyl cellobioside；β-Methyl-cellobiosid；Methyl 4-O-beta-D-glucopyranosyl-beta-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7216-73-1
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: FHNIYFZSHCGBPP-VJNWNIOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 methyl 4-O-methyl-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Crystal and molecular structure of methyl 4-O-methyl-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside

  摘要：

  The cellulose model compound methyl 4-O-inethyl-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside (6) was synthesised in high overall yield from methyl beta-D-cellobioside. The compound was crystallised from methanol to give colourless prisms, and the crystal structure was determined. The monoclinic space group is P2(1) with Z = 2 and unit cell parameters a = 6.6060 (13), b = 14.074 (3), c = 9.3180 (19) Angstrom, beta = 108.95(3)degrees. The structure was solved by direct methods and refined to R = 0.0286 for 2528 reflections. Both glucopyranoses occur in the C-4(1) chair conformation with endocyclic bond angles in the range of standard values. The relative orientation of both units described by the interglycosidic torsional angles [phi (O-5-C-1'-O-4-C-4:) -89.1degrees, phi (C-1'-O-4-C-4-C-5) - 152.0degrees] is responsible for the very flat shape of the molecule and is similar to those found in other cellodextrins. Different rotamers at the exocyclic hydroxymethyl group for both units are present. The hydroxymethyl group of the terminal glucose moiety displays a gauche-trans orientation, whereas the side chain of the reducing unit occurs in a gauche-gauche conformation. The solid state C-13 NMR spectrum of compound 6 exhibits all 14 carbon resonances. By using different cross polarisation times, the resonances of the two methyl groups and C-6 carbons can easily be distinguished. Distinct differences of the C-1 and C-4 chemical shifts in the solid and liquid states are found. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00299-3
• 作为产物：
  描述：

  α-cellobiose 在 sodium 、 溶剂黄146 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  [EN] COMPOUNDS FOR TREATING AND PREVENTING NET ASSOCIATED COMPLICATIONS
  [FR] COMPOSÉS POUR TRAITER ET PRÉVENIR DES COMPLICATIONS ASSOCIÉES AU NET

  摘要：

  本发明涉及具有高化学稳定性的化合物以及用于抑制受试者中NETs的病理活性的方法。具体而言，本发明涉及具有高化学稳定性的化合物，其用途以及用于抑制或改善NET介导的疾病（例如败血症、全身性免疫反应综合征（SIRS）和缺血再灌注损伤（IRI））的方法。更具体地，本发明涉及一种聚阴离子硫酸化的纤维二糖修饰物，其在其还原端具有一个小的不带电糖苷化链取代基，其中存在取代基导致分子具有高化学稳定性，而不影响分子在治疗NET介导的疾病中的有效性。例如，本发明涉及β-O-甲基纤维二糖硫酸酯（mCBS）或其药学上可接受的盐（例如mCBS.Na）的治疗方法和用途，用于治疗受试者中一系列NET介导的疾病。

  公开号：

  WO2020172698A1

文献信息

• Cellulase-catalysed, stereoselective synthesis of oligosaccharides
  作者：Shin-Ichiro Shoda、Kei Obata、Olaf Karthaus、Shiro Kobayashi

  DOI：10.1039/c39930001402

  日期：——

  Oligosaccharides are synthesised enzymatically using β-lactosyl fluoride as glycosyl donor and a variety of mono-, di-and tri-saccharides as acceptors; the nature of the active site of the catalyst cellulase is discussed on the basis of these reactions.

  低聚糖通过酶法合成，以β-乳糖基氟化物为糖基供体，多种单糖、二糖和三糖作为受体；根据这些反应，探讨了催化剂纤维素酶活性中心的性质。
• [EN] SULFATION METHOD<br/>[FR] PROCÉDÉ DE SULFATATION
  申请人：UNIV GRIFFITH

  公开号：WO2019113646A1

  公开（公告）日：2019-06-20

  A method of N- or O-sulfation of a compound is described whereby the use of a co-solvent system comprising a participating component and a non-participating component, during the sulfation reaction, allows for the non-participating component to actively sequester the participating component away from the sulfated reaction product. This has benefits in decreasing the likelihood or extent of desulfation of the sulfated product and may result in precipitation of the sulfated product thereby allowing for simple collection.

  描述了一种N-或O-硫酸化化合物的方法，其中在硫酸化反应过程中使用共溶剂系统，该系统包括参与组分和非参与组分，允许非参与组分将参与组分从硫酸化反应产物中主动分离。这有利于降低硫酸化产品脱硫的可能性或程度，并可能导致硫酸化产品的沉淀，从而可以简单收集。
• Inhibition of acid-catalyzed depolymerization of cellulose with boric acid in non-aqueous acidic media
  作者：Haruo Kawamoto、Shinya Saito、Shiro Saka

  DOI：10.1016/j.carres.2007.11.004

  日期：2008.2

  Boric acid inhibited the acid-catalyzed depolymerization of cellulose in sulfolane, a non-aqueous medium, at high temperature. Formation of the dehydration products such as levoglucosenone, furfural, and 5-hydroxymethyl furfural were also effectively inhibited. Similar inhibition was observed for cellooligosaccharides and starch, although the glucosidic bonds in methyl glucopyranosides and methyl cellobioside

  硼酸在高温下抑制环丁砜（一种非水介质）中纤维素的酸催化解聚。脱水产物如左旋葡萄糖醛酮，糠醛和5-羟甲基糠醛的形成也得到有效抑制。对于纤维寡糖和淀粉也观察到了相似的抑制作用，尽管甲基吡喃葡萄糖苷和甲基纤维二糖苷中的糖苷键被裂解形成了α-d-葡萄糖呋喃糖环状的1,2：3,5-双硼酸酯。
• Efficient one-pot per-O-acetylation–thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation–acetylation of S-/O-glycosides catalyzed by Mg(OTf)₂
  作者：Mana Mohan Mukherjee、Nabamita Basu、Aritra Chaudhury、Rina Ghosh

  DOI：10.1039/c6ra23198e

  日期：——

  A sequential one-pot per-O-acetylation–S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated

  据报道，在无溶剂条件下，使用0.5摩尔％的Mg（OTf）2作为非吸湿性，可循环利用的催化剂，对单糖和双糖进行连续一锅过O-乙酰化– S- / O-糖基化反应。糖苷和硫糖苷与苯甲醛或对甲氧基苯甲醛二甲基乙缩醛的区域选择性4,6- O-芳基化反应可通过10摩尔％的Mg（OTf）2催化生成相应的4,6- O-芳基化产物。Mg（OTf）2也可以高产率地介导单糖和二糖基糖苷和硫代糖苷的顺序一锅苯甲基化-乙酰化。
• Highly Efficient Synthesis of β(1 → 4)-Oligo- and -Polysaccharides Using a Mutant Cellulase
  作者：Sébastien Fort、Viviane Boyer、Lionel Greffe、Gideon J. Davies、Olga Moroz、Lars Christiansen、Martin Schülein、Sylvain Cottaz、Hugues Driguez

  DOI：10.1021/ja9936520

  日期：2000.6.1

  This report describes an efficient chemoenzymatic synthesis of a variety of regioselectively modified β(1→4)-oligo- and -polysaccharides. This successful approach was based on: (i) the use of a “glycosynthase” which is a Glu-197-Ala nucleophile mutant of the retaining cellulase endoglucanase I (Cel7B) from Humicola insolens and (ii) the rational design of modified acceptor and donor molecules through

  本报告描述了多种区域选择性修饰的 β(1→4)-寡糖和多糖的有效化学酶法合成。这种成功的方法基于：(i) 使用“糖合酶”，它是来自 Humicola insolens 的保留纤维素酶内切葡聚糖酶 I (Cel7B) 的 Glu-197-Ala 亲核突变体和 (ii) 修饰受体的合理设计和通过仔细检查野生型酶和突变酶的 X 射线结构给出的信息来确定供体分子。该突变体能够以高产率催化未取代和被各种单糖和二糖受体修饰的 α-糖二糖基氟的区域和立体选择性糖基化，以及通过单步反转机制聚合这些供体。