methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 155786-86-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranoside；methyl 2,3,6,2',3',6'-hexa-O-benzyl-β-cellobioside
• CAS: 155786-86-0
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: AOHOBOWOJXBEMI-XGOWSAFCSA-N

物化性质

• 沸点：
  923.4±65.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 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：

  甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3,6-tri-O-benzyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-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

文献信息

• β-Acarbose. VIII.The Synthesis of Some N-Linked Carba-Oligosaccharides
  作者：Matthew G. Tilbrook、Robert V. Stick、Spencer J. Williams

  DOI：10.1071/ch99031

  日期：——

  Two carbohydrate triflates have been used to alkylate a 1-epivalienamine derivative to give small amounts of the desired secondary amines, in addition to amounts of the products of elimination. Deprotection of the secondary amines afforded a carba-disaccharide and a carba-tetrasaccharide which have been shown to be good inhibitors of β-glucosidases.

  用两种碳水化合物三酸酯将 1-环戊二烯胺衍生物烷基化 衍生物进行烷基化，除得到少量所需的仲胺外 消除产物的数量。仲胺的脱保护 仲胺的脱保护作用可得到一种卡巴二糖和一种卡巴四糖。 这两种物质已被证明是 β-葡萄糖苷酶的良好抑制剂。
• Iron and Ruthenium Glycoporphyrins: Active Catalysts for the Synthesis of Cyclopropanes and Aziridines
  作者：Caterina Damiano、Sebastiano Gadolini、Daniela Intrieri、Luigi Lay、Cinzia Colombo、Emma Gallo

  DOI：10.1002/ejic.201900829

  日期：2019.11.10

  the synthesis of iron and ruthenium glycoporphyrins and their catalytic activity in promoting cyclopropanations and aziridinations by using diazo compounds and aryl azides as carbene and nitrene precursors, respectively. The number and location of carbohydrate units on the porphyrin skeleton modulated the shapeand diasteroselectivity of the reactions. Interestingly, while iron(III) glycoporphyrins

  鉴于环丙烷和氮丙啶作为合成结构单元以及生物和药物化合物中的活性部分的相关性，开发用于获得这些产品的可持续合成程序仍然是一项重大挑战。在此，我们报告了铁和钌糖卟啉的合成及其通过使用重氮化合物和芳基叠氮化物作为卡宾和氮烯前体分别促进环丙烷化和氮丙啶化的催化活性。卟啉骨架上碳水化合物单元的数量和位置调节了反应的形状和非对映选择性。有趣的是，虽然铁 (III) 糖卟啉在烯烃环丙烷化反应中表现出良好的性能，但钌 (II) 配合物在氮丙啶化反应中表现更好。
• 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。