dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside | 495394-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-dodecylsulfanyloxan-2-yl]methyl acetate
• CAS: 495394-47-3
• 化学式: C₂₆H₄₄O₉S
• 分子量: 532.696
• InChiKey: GQBQVSAIEXXNES-CAKRBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  36
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 在 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 dodecyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of α-series ganglioside GM1α containing C20-sphingosine

  摘要：

  A synthesis of alpha-series ganglioside GM1alpha(III6 Neu(5)AcGgOse(4)Cer) containing C20-sphingosine(d20:1) is described. Glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside with the glucosamine donor ethyl 3-O-acetyl-2-deoxy-4,6-O-[(4-methoxyphenyl)methylene]-2-phthalimido-1-thio-beta-D-glucopyranoside furnished a beta-(1-->4)-Iinked trisaccharide. Reductive cleavage of the p-methoxybenzylidene group followed by intramolecular inversion of its triflate afforded the desired trisaccharide, which was transformed into a trisaccharide acceptor via removal of the phthaloyl and O-acetyl groups followed by N-acetylation. A tetrasaccharide acceptor was obtained by glycosylation of the trisaccharide acceptor with dodecyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranoside, followed by removal of the p-methoxybenzyl group. Coupling of the tetrasaccharide acceptor with ethyl (methyl 4,7,8,9-tetra-0-acetyl-3,5-dideoxy-1-thio-5-trichloroacetamido-D-glycero-D-galacto-2-nonulopyranosid)onate and subsequent radical reduction gave the desired GM1alpha saccharide derivative, which was coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-eicosene-1,3-diol after conversion into the imidate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.023
• 作为产物：
  描述：

  2-(2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖基)异硫脲氢溴酸盐 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 dodecyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Characterization of some mesogenic alkyl 1-thioglycosides

  摘要：

  一系列十二烷基1-硫代-β-D-糖苷已经合成并表征（DSC、NMR、CP MAS、X射线衍射），作为可能具有液晶性质的新标记材料。这些化合物在不同温度下经历固体到液晶相转变，这取决于结构中碳水化合物部分的性质。它们的液晶相显示极端的剪切变薄行为。关键词：液晶、粉末X射线衍射、相变、硫代糖苷、固态NMR、标记材料

  DOI：

  10.1139/v02-157

文献信息

• Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis
  作者：Lajos Z. Szabó、Dillon J. Hanrahan、Evan M. Jones、Erin Martin、Jeanne E. Pemberton、Robin Polt

  DOI：10.1016/j.carres.2015.12.008

  日期：2016.3

  Here we report a method for the preparation of anomerically pure beta-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplen conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose

  在这里，我们报告了一种从相应的过乙酸盐供体制备异头纯β-S-吡喃糖苷（1,2-反式糖苷）的方法。在催化量的 InBr3 存在下，在 CHCl3 中回流进行 S-糖基化。在 Zemplen 条件下实现中间体过乙酸酯的脱酰化。五个吡喃糖的例子，单糖 D-葡萄糖和 D-半乳糖和二糖纤维二糖、麦芽糖和乳糖，被用作供体，五种硫醇，包括 α/ω 二硫醇和 Fmoc-L-半胱氨酸被用作受体。报告了先前未描述的化合物的熔点、高分辨率 MS、αD 和 NMR 数据((1)H 和 (13)C，包括 COSY、HSQC 和 HMBC)。
• Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics
  作者：Petr Džubák、Soňa Gurská、Kateřina Bogdanová、Daniela Uhríková、Nina Kanjaková、Sophie Combet、Tomáš Klunda、Milan Kolář、Marian Hajdúch、Monika Poláková

  DOI：10.1016/j.carres.2019.107905

  日期：2020.2

  as well as for antimicrobial potential on 12 bacterial and yeast strains. The most potent compounds were found to be tetradecyl and hexadecyl β-d-galactopyranosides (18, 19), which showed the best cytotoxicity and therapeutic index against CCRF-CEM cancer cell line. Similar cytotoxic activity showed hexadecyl α-d-mannopyranoside (5) but it also inhibited non-tumor cell lines. Because these two galactosides

  研究了一系列衍生自d-甘露糖，d-葡萄糖和d-半乳糖的，具有C10-C16糖苷配基的19种合成烷基和硫代烷基糖苷对7种人类癌症和2种非肿瘤细胞系的细胞毒活性以及抗菌潜力在12种细菌和酵母菌株上。发现最有效的化合物是十四烷基和十六烷基β-d-吡喃半乳糖苷（18、19），显示出对CCRF-CEM癌细胞系最佳的细胞毒性和治疗指数。相似的细胞毒活性显示十六烷基α-d-甘露吡喃糖苷（5），但它也抑制了非肿瘤细胞系。因为这两个半乳糖苷（18、19）对所有测试的细菌和酵母菌株均无活性，所以它们可能是真核细胞的靶标特异性靶标。另一方面，具有十四烷基（11）和十六烷基（12）糖苷配基的β-D-吡喃葡萄糖苷仅抑制革兰氏阳性菌粪肠球菌。从POPC模型膜上的SAXS实验推导，所研究的苷在高浓度下诱导脂质双层厚度和侧向相分离的变化。通常，葡糖苷和半乳糖苷表现出更具体的性质。具有较长糖苷配基的化合物显示出高细胞毒性，
• Synthesis of biotinylated keratan sulfate repeating disaccharides
  作者：Naoko Takeda、Jun-ichi Tamura

  DOI：10.1080/09168451.2014.877834

  日期：2014.1.2

  We synthesized four types of keratan and keratan sulfate repeating disaccharides containing non-sulfate, Galβ1-4GlcNAcβ, and three types of sulfates, Gal6Sβ1-4GlcNAcβ, Galβ1-4GlcNAc6Sβ, and Gal6Sβ1-4GlcNAc6Sβ in an efficient and stereo-controlled manner. These disaccharides were conjugated with biotin via a hydrophilic linker at the reducing terminal.

  我们以一种高效和立体控制的方式合成了四种类型的角质蛋白和角质蛋白硫酸盐重复二糖，其中包含非硫酸盐的Galβ1-4GlcNAcβ和三种硫酸盐，Gal6Sβ1-4GlcNAcβ、Galβ1-4GlcNAc6Sβ和Gal6Sβ1-4GlcNAc6Sβ。这些二糖通过一个亲水连接剂与生物素结合在还原末端。
• Synthetic construction of a Lex determinant via gabriel amine synthesis and the glycopolymer involving highly clustered Lex residues
  作者：Koji Matsuoka、Tatsuya Kohzu、Takashi Hakumura、Tetsuo Koyama、Ken Hatano、Daiyo Terunuma

  DOI：10.1016/j.tetlet.2009.03.099

  日期：2009.5

  Synthetic construction of a Lex determinant was accomplished via slightly modified Gabriel amine synthesis from three building blocks. Further transformations followed by polymerization of the Lex derivative gave a glycopolymer having trisaccharidic units as pendant-type epitopes.

  Le x决定簇的合成结构是通过从三个结构单元进行的稍加修饰的加百利胺合成而完成的。进一步的转化，随后勒的聚合X衍生物产生具有trisaccharidic单元作为侧链型表位的含糖。
• Synthesis of a tetrasaccharide repeating unit of O-antigenic polysaccharide of Salmonella enteritidis by use of unique and odorless dodecyl thioglycosyl donors
  作者：Sang-Hyun Son、Chiharu Tano、Tetsuya Furuike、Nobuo Sakairi

  DOI：10.1016/j.tetlet.2008.06.097

  日期：2008.9

  The first total synthesis of a unique tetrasaccharide repeating unit of lipopolysaccharide from Salmonella enteritidis has been accomplished by assembly of dodecyl thioglycosides. The crucial key steps were preparation of a rare branched dideoxy sugar, d-tyvelose (3,6-dideoxy-d-arabino-d-hexose) and sequential regioselective glycosylation at 2,3-positions of a central d-mannose residue 5 with d-tyvelose

  肠炎沙门氏菌的脂多糖独特的四糖重复单元的第一个全合成是通过组装十二烷基硫代糖苷完成的。关键的关键步骤是一种罕见的支链双脱氧糖，d-泰威糖（3,6-二脱氧D-的制备阿拉伯糖-d-己糖）和顺序的糖基化区域选择性的在中央d甘露糖残基的2,3位5与d-酪糖6和d-半乳糖供体7。