2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose | 151895-52-2

• 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: 2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose
• 英文别名: [(2S,3R,4R,5S,6S)-4,5-diacetyloxy-6-acetylsulfanyl-2-methyloxan-3-yl] acetate
• CAS: 151895-52-2
• 化学式: C₁₄H₂₀O₈S
• 分子量: 348.374
• InChiKey: WONRAJJGVBSKFV-CSHNMWLISA-N

物化性质

• 沸点：
  406.9±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.75h， 生成 n-propyl 4,6-di-O-acetyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-2-deoxy-3-thio-2-p-toluenesulfonamido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of α-L-fucopyranosyl disaccharides with thioglycosidic linkages and characterization of α-L-fucosidases from bovine kidney and epididymis by their inhibitory activities

  摘要：

  Sulfur-linked disaccharide analogs of three alpha-L-fucopyranosyl 2-acetamido-2-deoxy-beta-D-glucopyranosides and one alpha-L-fucopyranosyl beta-D-galactopyranoside were synthesized by substitution reactions of sulfonates and ring-opening reactions of aziridine as well as oxirane derivatives using 1-thio-alpha-L-fucopyranose as nucleophile. Fucosidases from bovine kidney and epididymis were inhibited by all of these disaccharide analogs and their Ki values range from 0.65 to 4.9 mM.

  DOI：

  10.1016/s0957-4166(00)80385-7
• 作为产物：
  描述：

  L-(-)-海藻糖 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 生成 2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose
  参考文献：
  名称：

  1→6,1→4和1→3连接的1-硫代-α-L-呋喃核糖基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和1→2连接的β-D-吡喃半乳糖苷的合成及其连接对α-L-岩藻糖苷酶的特异性抑制活性

  摘要：

  通过磺酸盐的取代反应和开环反应，合成了三种α-L-呋喃二糖基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷和一种α-L-呋喃二糖基β-D-吡喃半乳糖苷的硫连接二糖类似物。 1-硫代-α-L-呋喃琼脂糖衍生物作为亲核试剂测定氮丙啶和环氧乙烷衍生物。所有这些二糖类似物均抑制了来自牛肾和附睾的岩藻糖苷酶，其Ki值范围为0.65至4.9 mM。

  DOI：

  10.1016/s0040-4039(00)74055-x

文献信息

• Hexavalent thiofucosides to probe the role of the <i>Aspergillus fumigatus</i> lectin FleA in fungal pathogenicity
  作者：Christophe Dussouy、Pierre-Alban Lalys、Aurore Cabanettes、Victor Lehot、David Deniaud、Emilie Gillon、Viviane Balloy、Annabelle Varrot、Sébastien G. Gouin

  DOI：10.1039/d1ob00152c

  日期：——

  We designed hexavalent antagonists of the fucose-binding protein FleA from the pathogenic fungi A. fumigatus. An optimized chemical probe further evidenced the role of FleA in a fungistatic process mediated by epithelial cells.

  我们设计了对致病真菌A. fumigatus的富马糖结合蛋白FleA的六价拮抗剂。经过优化的化学探针进一步证实了FleA在由上皮细胞介导的抑菌过程中的作用。
• Improved Synthesis of 1‐Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues
  作者：Guang‐Jing Feng、Shuang‐Shuang Wang、Jian Lv、Tao Luo、Yuzhou Wu、Hai Dong

  DOI：10.1002/ejoc.202100357

  日期：2021.6.7

  We reported relative green synthesis of 1-thioglycosides by straightforward reaction of per-O-acetylated glycoses with KSAc in EtOAc. Furthermore, the highly efficient method to synthesize per-O-acetylated glycosyl disulfide and glycosyl 1-thiol were developed. Based on this, the synthesis of auranofin was improved and two thioglucoside gliflozin analogues (possible SGLT inhibitors) were efficiently

  我们报道的1-硫代糖苷相对绿色合成由per-的直接的反应Ó于EtOAc -acetylated葡糖与KSAc。此外，还开发了合成过氧乙酰化糖基二硫化物和糖基 1-硫醇的高效方法。在此基础上，金诺芬的合成得到改进，并以高产率高效合成了两种硫代葡萄糖苷格列净类似物（可能是 SGLT 抑制剂）。
• Synthesis and Biological Evaluation ofS-Neofucopeptides as E- and P-Selectin Inhibitors
  作者：Antonio J. Moreno-Vargas、Lidia Molina、Ana T. Carmona、Alessandro Ferrali、Martine Lambelet、Olivier Spertini、Inmaculada Robina

  DOI：10.1002/ejoc.200800199

  日期：2008.6

  The synthesis of α/β-L-fucosylated cysteamine, 3-thiopropionic acid, and 3-thioacetic acid derivatives as building blocks for the preparation of S-neofucopeptides is shown. These compounds were used in the synthesis of new thiofucosides derivatives (8α, 9α, 9β, 10α, 22α, 22β, 24α, 26α) that show affinity towards E- and P-selectins. They constitute a new series of hydrolytically stable and low-molecular-weight

  显示了 α/β-L-岩藻糖基化半胱胺、3-硫代丙酸和 3-硫代乙酸衍生物作为制备 S-新岩藻糖肽的构建块的合成。这些化合物用于合成新的硫代岩藻糖苷衍生物（8α、9α、9β、10α、22α、22β、24α、26α），这些衍生物对 E-和 P-选择蛋白具有亲和力。它们构成了天然 SLex 四糖的一系列新的水解稳定和低分子量模拟物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• [EN] MULTIVALENT FUCOSE DERIVATIVES FOR USE AS A DRUG<br/>[FR] DÉRIVÉS DE FUCOSE MULTIVALENTS DESTINÉS À ÊTRE UTILISÉS EN TANT QUE MÉDICAMENT
  申请人：UNIV NANTES

  公开号：WO2018149945A1

  公开（公告）日：2018-08-23

  The present invention relates to a compound bearing at least two fucose moieties for its use as a drug in the prevention or treatment of infections caused by Aspergillus spp, said compound having a molecular weight comprised from 0.6 to 340 kDa, in particular from 0.6 to 2 kDa or from 1 to 7 kDa or from 2 to 10 kDa or from 5 to 340 kDa.

  本发明涉及一种含有至少两个岩藻糖基团的化合物，用作预防或治疗由曲霉菌引起的感染的药物，所述化合物的分子量为0.6至340千道尔顿，特别是从0.6至2千道尔顿、从1至7千道尔顿、从2至10千道尔顿或从5至340千道尔顿。
• Drug design, synthesis, and evaluation of a non-sugar-based selectin antagonist
  作者：Kyoko Fukunaga、Takahiro Tsukida、Hideki Moriyama、Hirosato Kondo

  DOI：10.1016/s0960-894x(01)00430-9

  日期：2001.9

  We have designed a series of simple rigid compounds (2) having a phenyl ring attached to three essential groups necessary for selectin binding, i.e., a fucose unit, a carboxylic acid, and the hydrophobic part. In this series of compound 2, 2a exhibited strong inhibitory activity in in vitro P-selectin mediated cell adhesion assay. The novel type of compound 2a would be a potential lead compound for

  我们设计了一系列简单的刚性化合物（2），其苯环连接到选择素结合所必需的三个必需基团上，即岩藻糖单元，羧酸和疏水部分。在该系列化合物2、2a中，在体外P-选择蛋白介导的细胞粘附测定中显示出强抑制活性。新型化合物2a将成为选择素拮抗剂的潜在先导化合物。