4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside | 189744-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside
• 英文别名: (3aS,4R,6S,7R,7aR)-4-(2-methoxypropan-2-yloxymethyl)-2,2-dimethyl-6-(4-methylphenyl)sulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 189744-07-8
• 化学式: C₂₀H₃₀O₆S
• 分子量: 398.521
• InChiKey: FKNLZOXYTUCHCM-SFFUCWETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸 、 3 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， -45.0~90.0 ℃ 、101.33 kPa 条件下， 反应 15.63h， 生成 2-bromoethyl 2,3-di-O-acetyl-6,2'-O-methylidene-4-O-(3,4,6-tri-O-acetyl-α-D-galactropyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Restriction of Conformation in Galabiosides Via an O⁶−O²‘-Methylene Bridge

  摘要：

  Treatment of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (12) and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranoside (15) with the novel reagent combination formaldehyde diphenylmercaptal-N-iodosuccinimide-trifluoromethanesulfonic acid [(PhS)(2)CH2/NIS/TfOH], gave the corresponding 6,2'-O- and 4,6-O-methylidene acetals 13 and 16 in 52% and 53% yield, respectively. Deacetylation of 13 gave 2-(trimethylsilyl)ethyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (1). The conformation of 1 was similar to that of the non-acetalated parent glycoside.

  DOI：

  10.1021/jo962371x
• 作为产物：
  描述：

  4-甲基苯基2,3,4,6-四-O-乙酰基-1-硫代吡喃己糖苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 49.0h， 生成 4-methylphenyl 3,4-O-isoporpylidene-6-O-(2-methoxyisopropyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  使用自动聚糖装配法合成的植物阿拉伯半乳糖寡糖测定β1,4-内乳糖酶的底物特异性

  摘要：

  果胶是一种结构复杂的植物多糖，在食品中具有许多工业应用。果胶的结构阐明通过糖基水解酶的消化测定法得以辅助。我们报告了与果胶的阿拉伯半乳聚糖侧链有关的寡糖的自动聚糖组装，作为确定生化半乳糖苷酶底物特异性的新型生化工具。消化产物的分析揭示了对半乳糖酶识别和水解的寡糖的长度和阿拉伯糖取代模式的不同要求。

  DOI：

  10.1021/acs.joc.6b02745

文献信息

• Synthesis of Oligosaccharides Containing the <i>S</i>-Gal<i>p</i>(α1 → 3)Gal<i>p</i> Unit, Glycomimetic of the Epitope Recognized by Lytic Antibodies
  作者：Pablo Morrone-Pozzuto、María Laura Uhrig、Rosalia Agusti

  DOI：10.1021/acs.joc.2c01059

  日期：2022.10.21

  Two important activities take place in the surface of Trypanosoma cruzi, the agent of Chagas disease: the trans-sialidase (TcTS) catalyzes the transfer of sialic acid from the host glycoconjugates to the mucin-like glycoproteins from the parasite and the presence of lytic antibodies recognize the epitope α-Galp(1 → 3)-β-Galp(1 → 4)-α-GlcNAcp. This antigenic structure is known to be present in the parasite

  克氏锥虫（恰加斯病的病原体）的表面发生两项重要活动：转唾液酸酶 (TcTS) 催化唾液酸从宿主糖缀合物转移到寄生虫的粘蛋白样糖蛋白，以及裂解抗体的存在识别表位 α-Gal p (1 → 3)-β-Gal p (1 → 4)-α-GlcNAc p。已知这种抗原结构存在于寄生虫粘蛋白中；然而，为了成为转唾液酸酶的底物，一些半乳糖残基应该位于 β-Gal p配置。要研究这两种活动之间的相互作用，重要的是要计算合成结构以及结构相关的糖模拟物。为此，我们解决了含有 1 - S -α-Gal p (1 → 3)-β-Gal p基序的三糖和两个异构四糖的合成，这是裂解抗体识别的表位的硫类似物。从常见的乳糖前体开始，通过使用不同的活化供体进一步糖基化的半乳糖残基构型的双重反转来合并硫功能。通过高效阴离子交换色谱法测定，在 TcTS 催化的反应中，两种四糖都是唾液酸的良好受体。
• Synthesis of the Reducing‐end Hexasaccharide Fragment of Marine Lipopolysaccharide Axinelloside A
  作者：Haoliang Zhang、Changgen Zeng、Qian Zhu、Dapeng Zhu、Biao Yu

  DOI：10.1002/chem.202304180

  日期：2024.3.15

  reducing-end half of telomerase inhibitor axinelloside A was synthesized. Features of the synthetic approach include (1) preparation of the scyllo-inositol unit via Ferrier-type-II rearrangement, (2) formation of the 1,2-cis-glycosidic linkages via remote acyl group participation, and (3) concise [2+2+2] assembly by virtue of Au(I)-catalyzed glycosylation.

  合成了与端粒酶抑制剂 axinelloside A 的还原端半相关的适当保护的六糖。该合成方法的特点包括（1）通过Ferrier-II型重排制备鲨肌醇单元，（2）通过远程酰基参与形成1,2-顺式糖苷键，以及（3）简洁的[ 2+2+2]通过 Au(I) 催化的糖基化组装。
• Quantitative studies of the binding of the class II PapG adhesin from uropathogenic Escherichia coli to oligosaccharides
  作者：Andreas Larsson、Jörgen Ohlsson、Karen W Dodson、Scott J Hultgren、Ulf Nilsson、Jan Kihlberg

  DOI：10.1016/s0968-0896(03)00114-7

  日期：2003.5

  Binding of the class 11 PapG adhesin, found at the tip of filamentous pili on Escherichia coli, to the carbohydrate moiety of globoseries glycolipids in the human kidney is a key step in development of pyelonephritis, a severe form of urinary tract infection. An assay based on surface plasmon resonance for quantification of the binding of the class 11 PapG adhesin to oligosaccharides has been developed. Using this assay dissociation constants ranging from 80 to 540 muM were determined for binding of the PapG adhesin to di-pentasaccharide fragments from the globoseries of glycolipids. A series of galabiose derivatives, modified at the anomeric position, O-2' or O-3', was also investigated. The anomeric position appeared to be the most promising for development of improved inhibitors of PapG-mediated adhesion of E. coli. p-Methoxyphenyl galabioside was found to be most potent (K-d = 140 muM), and binds to PapG almost as well as the Forssman pentasaccharide. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly
  作者：Max P. Bartetzko、Frank Schuhmacher、Peter H. Seeberger、Fabian Pfrengle

  DOI：10.1021/acs.joc.6b02745

  日期：2017.2.3

  glycosyl hydrolases. We report the automated glycan assembly of oligosaccharides related to the arabinogalactan side chains of pectin as novel biochemical tools to determine the substrate specificities of endogalactanases. Analysis of the digestion products revealed different requirements for the lengths and arabinose substitution pattern of the oligosaccharides to be recognized and hydrolyzed by the

  果胶是一种结构复杂的植物多糖，在食品中具有许多工业应用。果胶的结构阐明通过糖基水解酶的消化测定法得以辅助。我们报告了与果胶的阿拉伯半乳聚糖侧链有关的寡糖的自动聚糖组装，作为确定生化半乳糖苷酶底物特异性的新型生化工具。消化产物的分析揭示了对半乳糖酶识别和水解的寡糖的长度和阿拉伯糖取代模式的不同要求。
• Restriction of Conformation in Galabiosides Via an <i>O</i>⁶−<i>O</i>²‘-Methylene Bridge
  作者：Michael Wilstermann、Joakim Balogh、Göran Magnusson

  DOI：10.1021/jo962371x

  日期：1997.5.1

  Treatment of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (12) and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranoside (15) with the novel reagent combination formaldehyde diphenylmercaptal-N-iodosuccinimide-trifluoromethanesulfonic acid [(PhS)(2)CH2/NIS/TfOH], gave the corresponding 6,2'-O- and 4,6-O-methylidene acetals 13 and 16 in 52% and 53% yield, respectively. Deacetylation of 13 gave 2-(trimethylsilyl)ethyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (1). The conformation of 1 was similar to that of the non-acetalated parent glycoside.