allyl L-fucoside | 242805-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl L-fucoside
• 英文别名: L-fucosyl-oxypropen；O-allyl-L-fucopyranose；(2S,3S,4R,5S)-2-methyl-6-prop-2-enoxyoxane-3,4,5-triol
• CAS: 242805-30-7
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: JPOJNSPEUPRVLQ-WAOFTFCCSA-N

物化性质

• 沸点：
  346.8±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl L-fucoside 在 甲醇 、 sodium hydride 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  合成新的 [(2S)-N-(p-Tolylsulfonyl)-2-Pyrrolidinyl]Propyl 2,3,4-Tri-O-Acetyl- 和 2,3,4-Tri-OBenzyl-β-L-Fucopyranosides

  摘要：

  合成两种新的糖杂环化合物 [(2lS*)-/V-(p-tolylsulfonyl)-2-pyrrolidinyl] 丙基 2,3,4-tri-Oacetyl 和 2,3,4-tri-O-benzyl-ß-描述了以 δ-氨基醇 (-)-[(2S)-N-(ptolylsulfonyl)-2-pyrrolidinyl]propan-l-ol 2 和 OaL-岩藻糖基三氯乙酰亚胺酯 3a 或 3b 作为糖基供体的 L-吡喃岩藻糖苷 1a 和 lb . 迄今为止，δ-氨基醇 2 是由 L-脯氨酸合成的，在其制备过程中没有任何外消旋化。

  DOI：

  10.1515/hc.2010.16.2-3.105
• 作为产物：
  描述：

  6-deoxy-L-galactose 、 烯丙醇 在 Amberlite IR 120 (H⁺) 作用下， 反应 4.0h， 生成 allyl L-fucoside
  参考文献：
  名称：

  酚醛糖苷的合成：通过双光催化氧化/镍催化糖基糖醇与芳基溴化物的糖基化

  摘要：

  通过在可见光下用Ir [dF（CF 3）ppy] 2（dtbbpy）（PF 6）作为光催化剂在乙腈中用芳基溴化物处理，将多种糖乳糖醇有效地转化为相应的酚类糖苷。在温和的反应条件下，吡喃糖酶和呋喃糖酶甚至二糖都可能遭受这种糖基化方案的影响。可以以中等到良好的产率（高达93％的产率）生产各种苯基糖苷，并且该方案的克级工艺也得到了很好的确立。

  DOI：

  10.1021/acs.joc.8b02129

文献信息

• Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
  作者：Christine Wiebe、Claudine Schlemmer、Stefan Weck、Till Opatz

  DOI：10.1039/c1cc13078a

  日期：——

  Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

  单糖基和二糖基修饰的芳香化合物和杂芳香化合物可作为构建代谢稳定的低聚糖模拟物的砌块。本文描述了通过直接C-糖基化、偶极环加成或Larock环化反应从单糖前体合成这些化合物的方法。
• The synthesis of heterosaccharides related to the fucoidan from Chordaria flagelliformis bearing an α-<scp>l</scp>-fucofuranosyl unit
  作者：Dmitry Z. Vinnitskiy、Vadim B. Krylov、Nadezhda E. Ustyuzhanina、Andrey S. Dmitrenok、Nikolay E. Nifantiev

  DOI：10.1039/c5ob02040a

  日期：——

  fucoidans, from brown algae are built up mainly of α-L-fucopyranosyl units and form a group of natural biopolymers with a wide spectrum of biological activities. Systematic synthesis of oligosaccharides representing fucoidans’ fragments gives molecular probes for detecting pharmacophores within fucoidan polysaccharide chains. Recently, it was discovered that the fucoidan from brown seaweed Chordaria

  来自褐藻的硫酸化多糖岩藻依聚糖主要由α- L-吡喃岩藻糖基单元构成，形成一组具有广谱生物活性的天然生物聚合物。代表岩藻依聚糖片段的寡糖的系统合成为检测岩藻依聚糖多糖链内的药效团提供了分子探针。最近发现，来自褐藻Chordaria flagelliformis的岩藻依聚糖不仅含有α- L-吡喃岩藻糖基单元，还含有α- L-呋喃岩藻糖基单元。为了确定不寻常的α- L-岩藻糖残基对岩藻依聚糖的生物活性和构象特性的影响，进行了选择性O-硫酸化五糖的合成，其代表来自鞭毛藻的岩藻依聚糖的主要重复单元。该合成的特点是利用吡喃糖苷重排制备呋喃糖苷前体，并远程立体控制O-酰基的参与来控制糖基化反应中立体选择性α-键的形成。
• An abnormal deallylation reaction of an l-fucopyranoside
  作者：Zhong-Jun Li、Hui Li、Yi-Ping Lu、Xu-Ling Shi、Meng-Shen Cai

  DOI：10.1016/s0008-6215(99)00055-5

  日期：1999.4

  Deallylation of allyl 2,3,4-tri-O-benzyl-L-fucopyranoside in the presence of palladium chloride and cuprous chloride led to an unexpected result. Instead of the expected deallylated product, (2-oxopropyl)-2,3,4-tri-O-benzyl-L-fucopyranoside was obtained. (C) 1999 Elsevier Science Ltd. AII rights reserved.
• Potential use of fucose-appended dendrimer/α-cyclodextrin conjugates as NF-κB decoy carriers for the treatment of lipopolysaccharide-induced fulminant hepatitis in mice
  作者：Chiho Akao、Takahiro Tanaka、Risako Onodera、Ayumu Ohyama、Nana Sato、Keiichi Motoyama、Taishi Higashi、Hidetoshi Arima

  DOI：10.1016/j.jconrel.2014.07.004

  日期：2014.11

  The purpose of the present study is to treat lipopolysaccharide (LPS)-induced fulminant hepatitis by NF-kappa B decoy complex with fucose-appended dendrimer (generation 2; G2) conjugate with alpha-cyclodextrin (Fuc-S-alpha-CDE (G2)). Fuc-S-alpha-CDE (G2, average degree of substitution of fucose (DSF2))/NF-kappa B decoy complex significantly suppressed nitric oxide and tumor necrosis factor-alpha (TNF-alpha) production from LPS-stimulated NR8383 cells, a rat alveolar macrophage cell line, by adequate physicochemical properties and fucose receptor-mediated cellular uptake. Intravenous injection of Fuc-S-alpha-CDE (G2, DSF2)/NF-kappa B decoy complex extended the survival of LPS-induced fulminant hepatitis model mice. In addition, Fuc-S-alpha-CDE (G2, DSF2)/NF-kappa B decoy complex administered intravenously highly accumulated in the liver, compared to naked NF-kappa B decoy alone. Furthermore, the liver accumulation of Fuc-S-alpha-CDE (G2, DSF2)/NF-kappa B decoy complex was inhibited by the pretreatment with GdCl3, a specific inhibitor of Kupffer cell uptake. Also, the serum aspartate aminotransferase, alanine aminotransferase and TNF-alpha levels in LPS-induced fulminant hepatitis model mice were significantly attenuated by the treatment with Fuc-S-alpha-CDE (G2, DSF2)/NF-kappa B decoy complex, compared with naked NF-kappa B decoy alone. Taken together, these results suggest that Fuc-S-alpha-CDE (G2, DSF2) has the potential for a novel Kupffer cell-selective NF-kappa B decoy carrier for the treatment of LPS-induced fulminant hepatitis in mice. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis
  作者：Hui Ye、Cong Xiao、Quan-Quan Zhou、Peng George Wang、Wen-Jing Xiao

  DOI：10.1021/acs.joc.8b02129

  日期：2018.11.2

  Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irradiation. Both pyranoses and furanoses or even disaccharide could all suffer this glycosylation protocol under mild reaction conditions. A variety of phenyl glycosides can be produced

  通过在可见光下用Ir [dF（CF 3）ppy] 2（dtbbpy）（PF 6）作为光催化剂在乙腈中用芳基溴化物处理，将多种糖乳糖醇有效地转化为相应的酚类糖苷。在温和的反应条件下，吡喃糖酶和呋喃糖酶甚至二糖都可能遭受这种糖基化方案的影响。可以以中等到良好的产率（高达93％的产率）生产各种苯基糖苷，并且该方案的克级工艺也得到了很好的确立。