ethyl 3-O-methyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-methyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 4,6-O-benzylidene-3-O-methyl-1-thio-β-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aR)-6-ethylsulfanyl-8-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• 化学式: C₁₆H₂₂O₅S
• 分子量: 326.414
• InChiKey: WFVNREYTTGWFFS-SJJUBHFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-methyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， -15.0~20.0 ℃ 、275.8 kPa 条件下， 反应 94.0h， 生成
  参考文献：
  名称：

  Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties

  摘要：

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.

  DOI：

  10.1021/jacs.8b11882
• 作为产物：
  描述：

  Ethyl 2,4,6-tri-O-acetyl-3-O-methyl-1-thio-β-D-glucopyranoside 在 甲醇 、 sodium methylate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 ethyl 3-O-methyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties

  摘要：

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.

  DOI：

  10.1021/jacs.8b11882

文献信息

• A Concise Synthesis of the Repeating Unit of Capsular Polysaccharide <i>Staphylococcus aureus</i> Type 8
  作者：Satsawat Visansirikul、Jagodige P. Yasomanee、Papapida Pornsuriyasak、Medha N. Kamat、Nikita M. Podvalnyy、Chase P. Gobble、Melissa Thompson、Stephen A. Kolodziej、Alexei V. Demchenko

  DOI：10.1021/acs.orglett.5b00899

  日期：2015.5.15

  The first synthesis of the repeating unit of S. aureus capsular polysaccharide type 8 is described. The repeating unit is an unusual trisaccharide sequence of three uncommon sugars, all connected via 1,2-cis linkages. The synthetic trisaccharide was equipped with capping methyl groups at the points of propagation of the polysaccharide sequence.
• Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-d-gluco- and galactopyranosides displaying a range of anomeric substituents
  作者：Helen M.I Osborn、Victoria A Brome、Laurence M Harwood、William G Suthers

  DOI：10.1016/s0008-6215(01)00063-5

  日期：2001.5

  The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-beta -D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-d-glucopyranoside, derivatives displaying a range of anomeric substituents
  作者：Jonathan J. Gridley、Helen M.I. Osborn、William G. Suthers

  DOI：10.1016/s0040-4039(99)01420-3

  日期：1999.9

  Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, phenyl 4,6-O-benzylidene-beta-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-beta-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Oligosaccharides Self-Assemble and Show Intrinsic Optical Properties
  作者：Yang Yu、Soeun Gim、Dongyoon Kim、Zohar A. Arnon、Ehud Gazit、Peter H. Seeberger、Martina Delbianco

  DOI：10.1021/jacs.8b11882

  日期：2019.3.27

  Self-assembling peptides and oligonucleotides have given rise to synthetic materials with several applications in nanotechnology. Aggregation of synthetic oligosaccharides into well-defined architectures has not been reported even though natural polysaccharides, such as cellulose and chitin, are key structural components of biomaterials. Here, we report that six synthetic oligosaccharides, ranging from dimers to hexamers, self-assemble into nanostructures of varying morphologies and emit within the visible spectrum in an excitation-dependent manner. Well-defined differences in chain length, monomer modification, and aggregation methods yield glycomaterials with distinct shapes and properties. The excitation-dependent fluorescence in a broad range within the visible spectrum illustrates their potential for use in optical devices and imaging applications. We anticipate that our systematic approach of studying well-defined synthetic oligosaccharides will form the foundation of our understanding of carbohydrate interactions in nature.