2,3,4-tri-O-acetyl-1-O-propargyl-α-L-fucose | 1307677-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-1-O-propargyl-α-L-fucose
• 英文别名: 2,3,4-tri-O-acetyl-1-O-propargyl-L-fucose；propargyl L-fucopyranoside；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-2-methyl-6-prop-2-ynoxyoxan-3-yl] acetate
• CAS: 1307677-45-7
• 化学式: C₁₅H₂₀O₈
• 分子量: 328.319
• InChiKey: WVHFUGQYVRPIGA-KVOGPGQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1-O-propargyl-α-L-fucose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以81%的产率得到
  参考文献：
  名称：

  Development of α1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

  摘要：

  We developed alpha 1,6-fucosyltransferase (FUT8) inhibitors through a diversity-oriented synthesis. The coupling reaction between the fucose unit containing alkyne and the guanine unit containing sulfonyl azide under various conditions afforded a series of Guanosine 5'-diphospho-beta-L-fucose (GDP-fucose) analogs. The synthesized compounds displayed FUT8 inhibition activity. A docking study revealed that the binding mode of the inhibitor synthesized with FUT8 was similar to that of GDP-fucose. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.036
• 作为产物：
  描述：

  、 2-丙炔-1-醇 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以54%的产率得到2,3,4-tri-O-acetyl-1-O-propargyl-α-L-fucose
  参考文献：
  名称：

  Development of α1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

  摘要：

  We developed alpha 1,6-fucosyltransferase (FUT8) inhibitors through a diversity-oriented synthesis. The coupling reaction between the fucose unit containing alkyne and the guanine unit containing sulfonyl azide under various conditions afforded a series of Guanosine 5'-diphospho-beta-L-fucose (GDP-fucose) analogs. The synthesized compounds displayed FUT8 inhibition activity. A docking study revealed that the binding mode of the inhibitor synthesized with FUT8 was similar to that of GDP-fucose. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.036

文献信息

• Fullerene sugar balls
  作者：Jean-François Nierengarten、Julien Iehl、Vincent Oerthel、Michel Holler、Beatriz M. Illescas、Antonio Muñoz、Nazario Martín、Javier Rojo、Macarena Sánchez-Navarro、Samy Cecioni、Sébastien Vidal、Kevin Buffet、Maxime Durka、Stéphane P. Vincent

  DOI：10.1039/c0cc00034e

  日期：——

  Fullerene hexakis-adducts bearing 12 peripheral carbohydrate moieties have been prepared by grafting sugar derivatives onto the fullerene core through the copper mediated Huisgen 1,3-dipolar cycloaddition of azides and alkynes.

  通过铜介导的叠氮化物和炔烃的 Huisgen 1,3- 二极环化反应，将糖衍生物接枝到富勒烯核心上，制备出含有 12 个外围碳水化合物分子的富勒烯六烷基加合物。
• Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on <i>N</i> ‐Alkylation of <i>N</i> ‐Acylhydrazone
  作者：Marwa Fray、David Mathiron、Serge Pilard、David Lesur、Rym Abidi、Thouraya Barhoumi‐Slimi、Peter J. Cragg、Mohammed Benazza

  DOI：10.1002/ejoc.202101537

  日期：2022.9.6

  We report a new orthogonal strategy involving the N-alkylation of N-acylhydrazone as a key step. When followed by azido-alkyne click chemistry, it represents a new and straightforward synthetic method to prepare N-alkyl-NAH glycoconjugates of small molecules, heterodisaccharides, and heteroglycoclusters-based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties

  我们报告了一种新的正交策略，其中 N-酰基腙的N-烷基化是关键步骤。紧随其后的是叠氮基-炔烃点击化学，它代表了一种新的、直接的合成方法，用于制备基于锥 p - t Bu-calix[4] 芳烃和 1的小分子、杂二糖和杂糖簇的N-烷基-NAH 糖缀合物， 3- alt p - t Bu-thiacalix[4] 芳烃，具有潜在的药物样特性。
• Systematic Strategy for the Development of Glycosyltransferase Inhibitors: Diversity-Oriented Synthesis of FUT8 Inhibitors
  作者：Yoshiyuki Manabe、Koichi Fukase、Koki Hizume、Yohei Takakura、Shinji Takamatsu、Eiji Miyoshi、Yoshihiro Kamada、Ramón Hurtado-Guerrero

  DOI：10.1055/a-2221-9096

  日期：——

  we investigated the development of FUT8 inhibitors with structural elements encompassing both the glycosyl donor (GDP-fucose) and acceptor (N-glycan) of FUT8. To efficiently optimize the structure of FUT8 inhibitors, we employed a strategy involving fragmentation of the target structure, followed by a structure optimization using a diversity-oriented synthesis approach. This study proposes an efficient

  聚糖根据其结构控制各种生物过程。特别是，由 α1,6-岩藻糖基转移酶 (FUT8) 形成的核心岩藻糖对多种生物过程具有重大影响。在这项研究中，我们研究了 FUT8 抑制剂的开发，其结构元件包含 FUT8 的糖基供体（GDP-岩藻糖）和受体（N-聚糖）。为了有效优化 FUT8 抑制剂的结构，我们采用了一种策略，包括目标结构的片段化，然后使用面向多样性的合成方法进行结构优化。这项研究提出了一种加速中间分子结构优化的有效策略。
• Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists
  作者：Vishal Kumar Rajput、Hakon Leffler、Ulf J. Nilsson、Balaram Mukhopadhyay

  DOI：10.1016/j.bmcl.2014.05.063

  日期：2014.8

  A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4 N, -4C, -7, -8 N, -9 N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8 N, and 9 N with up to 40-fold affinity enhancements relative to methyl alpha-D-galactopyranoside due to the coumarylmethyl moieties. (C) 2014 Elsevier Ltd. All rights reserved.