methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside | 156038-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: methyl 4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranoside；methyl 4',6'-O-benzylidene-β-cellobioside
• CAS: 156038-69-6
• 化学式: C₂₀H₂₈O₁₁
• 分子量: 444.436
• InChiKey: GTNTZHZBKDWTBH-ZXSUYJAKSA-N

物化性质

• 熔点：
  275 °C (decomp)(Solv: ethanol (64-17-5); chloroform (67-66-3))
• 沸点：
  702.8±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  156.53
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 、 sodium cyanoborohydride 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：

  纤维素二糖 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4,6-O-benzylidene-β-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Some Approaches to Glycosylated Versions of Methyl β-Acarviosin

  摘要：

  甲基 β-arviosin "是纤维素酶的一种假定抑制剂，在研究 "甲基 β-arviosin "糖基化版本的第一种方法中，纤维生物糖被转化为一种碳环烯酮，而这种碳环烯酮无法转化为后续烷基化所需的胺。另一种方法是使用 "糖合成酶 "在 C4′处对甲基 β-arviosin 本身进行糖基化，以提供 "三糖"（和一些 "四糖"）。这两种分子都是各种纤维素酶的有效抑制剂。在研究上述 "三糖 "的异构体的相关方法中，1-表戊二烯胺的选择性保护衍生物与碳水化合物三酸酯发生烷基化反应，得到了一种 "二糖"，但这种 "二糖 "不能通过糖基化反应得到所需的 "三糖"。报告中还提到了另一种处理该分子的失败方法。

  DOI：

  10.1071/ch03203

文献信息

• 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。
• Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lectins
  作者：Paloma Fernández、Jesús Jiménez-Berbero、Manuel Martín-Lomas

  DOI：10.1016/0008-6215(94)84243-4

  日期：1994.2

  The synthesis of all the possible monomethyl ethers of methyl beta-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6,3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur

  甲基β-内酯（1）的所有可能的单甲基醚的合成已从1直接进行，利用了烷基化和甲锡烷基化反应中羟基的不同反应性。另外，通过适当的底物与二乙基氨基三氟化硫或氟化四丁基铵的反应制备了在6,3'，4'，epi-4'和6'位置的1的脱氧氟衍生物。最后，还制备了1的6-脱氧碘和6'-溴脱氧氧基类似物。
• Synthetic Phosphoethanolamine Cellobiose Promotes <i>Escherichia coli</i> Biofilm Formation and Congo Red Binding
  作者：Johny M. Nguyen、Rebecca E. Moore、Sabrina K. Spicer、Jennifer A. Gaddy、Steven D. Townsend

  DOI：10.1002/cbic.202000869

  日期：——

  A phosphoethanolamine (pEtN) cellobiose was synthesized and evaluated for its effects on E. coli biofilms . The impact of the synthetic disaccharide on biofilm formation was examined via colorimetric assays revealing an increase in cellular adhesion to an abiotic substrate. Congo red binding assays indicate that culturing E. coli in the presence of pEtN cellobiose enhances Congo red binding to bacterial

  合成了磷酸乙醇胺(pEtN) 纤维二糖并评估了其对大肠杆菌生物膜的影响。通过比色测定检查了合成二糖对生物膜形成的影响，结果显示细胞对非生物基质的粘附增加。刚果红结合测定表明，在 pEtN 纤维二糖存在下培养大肠杆菌可增强刚果红与细菌细胞的结合。最后，单电子显微镜显示二糖增加了卷曲纤维的产生。
• Simple syntheses of 4-O-glucosylated 1-deoxynojirimycins from maltose and cellobiose
  作者：Andreas J. Steiner、Arnold E. Stütz

  DOI：10.1016/j.carres.2004.07.022

  日期：2004.10

  Glucosidase inhibitors alpha-D-glucopyranosyl-(1-->4)-1-deoxynojirimycin and beta-D-glucopyranosyl-(1-->4)-1-deoxynojirimycin were prepared from maltose and cellobiose, respectively, via the corresponding 5,6-eno derivatives, their epoxidation and the subsequent double reductive amination of the resulting 5-uloses. In both cases, the reported route is the first chemical synthesis not based on enzymatic

  分别由麦芽糖和纤维二糖分别通过相应的5种糖苷酶抑制剂α-D-葡萄糖吡喃糖基-（1-> 4）-1-脱氧野rim霉素，6-eno衍生物，其环氧化作用和随后的双还原胺化生成的5-uloses。在这两种情况下，报道的途径都是不基于酶促葡萄糖基转移的第一化学合成。