((2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate | 53756-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate
• 英文别名: methyl 2-acetamido-2-deoxy-6-O-p-tolylsulfonyl-α-D-glucopyranoside；methyl 6-O-p-tolylsulfonyl-2-acetamido-2-deoxy-α-D-glucopyranoside；methyl 2-acetamido-2-deoxy-6-O-tosyl-α-D-glucopyranoside；Methyl-2-acetamido-2-deoxy-6-O-tosyl-α-D-glucopyranosid；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 53756-24-4
• 化学式: C₁₆H₂₃NO₈S
• 分子量: 389.427
• InChiKey: ONMQOJFQBLJDIM-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到methyl 2-acetamido-3,6-anhydro-2-deoxy-α-D-glucofuranoside
  参考文献：
  名称：

  Furanodictine A和B：细胞粘液霉菌盘基网柄菌产生的氨基糖类似物，显示神经元分化活性。

  摘要：

  我们调查了盘基网柄菌的成分，以阐明盘基网柄细胞粘液霉菌的次生代谢产物的多样性，并探索可用于开发新药的生物活性物质。从D. discoideum的多细胞子实体的甲醇提取物中，我们分离了两个新的氨基糖类似物，呋喃果苦碱A（1）和B（2）。它们是最早从天然来源中分离出来的3,6-脱水糖。通过光谱方法阐明了它们的相对结构，并通过1和2的不对称合成证实了其绝对构型。这些呋喃西汀可有效诱导大鼠嗜铬细胞瘤（PC-12）细胞的神经元分化。

  DOI：

  10.1021/jo015657x
• 作为产物：
  描述：

  methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 ((2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Furanodictine A和B：细胞粘液霉菌盘基网柄菌产生的氨基糖类似物，显示神经元分化活性。

  摘要：

  我们调查了盘基网柄菌的成分，以阐明盘基网柄细胞粘液霉菌的次生代谢产物的多样性，并探索可用于开发新药的生物活性物质。从D. discoideum的多细胞子实体的甲醇提取物中，我们分离了两个新的氨基糖类似物，呋喃果苦碱A（1）和B（2）。它们是最早从天然来源中分离出来的3,6-脱水糖。通过光谱方法阐明了它们的相对结构，并通过1和2的不对称合成证实了其绝对构型。这些呋喃西汀可有效诱导大鼠嗜铬细胞瘤（PC-12）细胞的神经元分化。

  DOI：

  10.1021/jo015657x

文献信息

• Studies toward the synthesis of linear triazole linked pseudo oligosaccharides and the use of ferrocene as analytical probe
  作者：Magnus S. Schmidt、Kathrin H. Götz、Wolfgang Koch、Tanja Grimm、Markus Ringwald

  DOI：10.1016/j.carres.2016.03.005

  日期：2016.4

  different building blocks have been synthesised and used for the synthesis of linear triazole linked pseudo oligosaccharides with copper(I)-catalysed cycloaddition (CuAAC). Ethynylferrocene has been used as analytical probe to improve the UV/Vis properties and HPLC methods have been used and optimised for the analysis of the pseudo oligosaccharides. The smallest ones have been isolated and characterised by

  已经合成了三种不同的结构单元，并用于铜（I）催化的环加成反应（CuAAC）合成线性三唑连接的假寡糖。乙炔基二茂铁已被用作分析探针以改善UV / Vis特性，并且HPLC方法已被使用和优化用于伪寡糖的分析。最小的已被分离，并通过分析型HPLC，NMR，ESI-MS和元素分析进行​​了表征。
• A new class of nitrosoureas. IX. Synthesis and antitumor activity of 3-substituted 1-(2-chloroethyl)-3-(methyl .ALPHA.-D-glucopyranosid-6-yl or methyl 2-acetamido-2-deoxy-.ALPHA.-D-glucopyranosid-6-yl)-1-nitrosoureas.
  作者：TAMIO MORIKAWA、KENJI TSUJIHARA、MIKIO TAKEDA、YOSHIHISA ARAI

  DOI：10.1248/cpb.31.3924

  日期：——

  A series of eight 3, 3-disubstituted nitrosoureas (IVa-h) having the nitrosoureido group at the C-6 position of methyl glucopyranoside or methyl 2-acetamido-2-deoxy-glucopyranoside was prepared and tested for antitumor activities. Heating of the 6-O-p-tolylsulfonyl derivatives (I and II) with various alkylamines followed by reaction with 2-chloroethyl isocyanate gave the corresponding ureas (IIIa-h), which were nitrosated with nitrogen tetroxide to give IVa-h in high yields. The nitrosoureas (IVa-h) were significantly less active than the other positional isomers with respect to the nitrosoureido group prepared previously. Compounds IVa-h appear to be activated by a γ hydroxyl group at the C-4 position. The rate of activation, however, proved to be much slower than those of the C-1 or C-3 positional isomers having a β hydroxyl group. The structure-activity relationships of the positional isomers are discussed in the light of this difference in the rate of activation.

  一系列八种3, 3-二取代的亚硝基脲化合物（IVa-h）被合成，并在甲基葡萄糖吡喃糖或甲基2-乙酰氨基-2-脱氧葡萄糖吡喃糖的C-6位点上具有亚硝基脲基团，随后进行抗肿瘤活性测试。将6-O-对甲苯磺酰基衍生物（I和II）与各种烷基胺加热反应，随后与2-氯乙基异氰酸酯反应，得到了相应的脲（IIIa-h），这些脲与四氧化二氮进行亚硝化反应，得到IVa-h，产率很高。与之前合成的其他位置异构体相比，亚硝基脲（IVa-h）的活性明显较低。IVa-h化合物似乎通过C-4位置的γ羟基团被激活。然而，激活速度证明明显慢于具有β羟基团的C-1或C-3位置异构体。根据这一激活速率的差异，讨论了位置异构体的结构-活性关系。
• Triazole Linked <i>N</i>-Acetylglucosamine Based Gelators for Crude Oil Separation and Dye Removal
  作者：Chintam Narayana、Priti Kumari、Ghanshyam Tiwari、Ram Sagar

  DOI：10.1021/acs.langmuir.9b02704

  日期：2019.12.24

  Recently, phase selective organo-gelators emerged as potential materials for removal of oil from water through selective gelation. Herein, we report synthesis of a series of C-6 triazole linked N-acetylglucosamine derivatives, among which three have shown excellent selective gelation of organic solvents, diesel, petrol, and crude oils in water and seawater. We have studied phase selective gelation against

  海洋溢油对环境具有长期影响；因此，寻找补救的解决方案是科学界的主要关注。近来，相选择有机胶凝剂作为通过选择性胶凝从水中除去油的潜在材料而出现。本文中，我们报道了一系列C-6三唑连接的N-乙酰氨基葡糖衍生物的合成，其中三个在水和海水中显示出优异的有机溶剂，柴油，汽油和原油的选择性凝胶化效果。我们已经研究了针对不同API级原油（从轻到重）的相选择性凝胶化，并且在室温下使用无毒载体溶剂在不到15分钟的时间内实现了凝胶化，发现凝胶剂可用于回收原油。发现原油胶凝剂的临界胶凝浓度（CGC）为2。3-12％（w / v）。可变温度NMR和FTIR实验表明，分子间氢键是凝胶形成的原因。此外，使用胶凝剂从水中选择性去除染料。
• Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists
  作者：Sabine Borowski、Dirk Michalik、Helmut Reinke、Christian Vogel、Anna Hanuszkiewicz、Katarzyna A. Duda、Otto Holst

  DOI：10.1016/j.carres.2008.02.001

  日期：2008.5

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.
• Furanodictine A and B:  Amino Sugar Analogues Produced by Cellular Slime Mold <i>Dictyostelium </i><i>d</i><i>iscoideum</i> Showing Neuronal Differentiation Activity
  作者：Haruhisa Kikuchi、Yoshinori Saito、Jun Komiya、Yoshiaki Takaya、Shigeyoshi Honma、Norimichi Nakahata、Akira Ito、Yoshiteru Oshima

  DOI：10.1021/jo015657x

  日期：2001.10.1

  We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2).

  我们调查了盘基网柄菌的成分，以阐明盘基网柄细胞粘液霉菌的次生代谢产物的多样性，并探索可用于开发新药的生物活性物质。从D. discoideum的多细胞子实体的甲醇提取物中，我们分离了两个新的氨基糖类似物，呋喃果苦碱A（1）和B（2）。它们是最早从天然来源中分离出来的3,6-脱水糖。通过光谱方法阐明了它们的相对结构，并通过1和2的不对称合成证实了其绝对构型。这些呋喃西汀可有效诱导大鼠嗜铬细胞瘤（PC-12）细胞的神经元分化。