(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne | 287962-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne
• 英文别名: 3,4-anhydro-4,5,6,8-tetra-O-benzyl-1,2-dideoxy-D-glycero-L-gluco-oct-1-ynitol；(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyl-tetrahydropyran；1-α-ethynyl-2,3,4,6-tetra-O-benzyl-D-galactose；(2R,3S,4R,5S,6R)-2-ethynyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 287962-77-0
• 化学式: C₃₆H₃₆O₅
• 分子量: 548.679
• InChiKey: ODYZSGODFGXEDP-DQROVBKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne 在 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以85%的产率得到(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethene
  参考文献：
  名称：

  实用的C-乙烯基糖苷的α-或β-异构体的克级合成

  摘要：

  抽象的 合成Ç -乙烯基苷，有用的中间体用于合成Ç -glycoconjugates，通过在良好对应的乙炔基衍生物的受控降低上进行克级在不同的碳水化合物系列优异的产率。 合成Ç -乙烯基苷，有用的中间体用于合成Ç -glycoconjugates，通过在良好对应的乙炔基衍生物的受控降低上进行克级在不同的碳水化合物系列优异的产率。

  DOI：

  10.1055/s-0037-1611800
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 potassium fluoride 、 18-冠醚-6 、 硫酸 、 水 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.92h， 生成 (2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyne
  参考文献：
  名称：

  Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases

  摘要：

  该发明涉及以下化合物的新颖化合物：其中X为O或NH；R3为OH或单糖，R4为氢，或R3为氢，R4为OH或单糖；R5为氢或单糖；以及其药用盐或酯。该发明还涉及这些化合物的直接使用以及作为免疫佐剂用于治疗癌症、传染病和自身免疫疾病。该发明还涉及合成这些中间体的方法，这些中间体可用于制备这些新颖化合物。

  公开号：

  US20050222048A1

文献信息

• Synthesis of 1,2,3-triazole linked galactopyranosides and evaluation of cholera toxin inhibition
  作者：David J. Leaver、Raymond M. Dawson、Jonathan M. White、Anastasios Polyzos、Andrew B. Hughes

  DOI：10.1039/c1ob06317k

  日期：——

  We report the synthesis of a series of bivalent 1,2,3-triazole linked galactopyranosides as potential inhibitors of cholera toxin (CT). The inhibitory activity of the bivalent series was examined (ELISA) and the series showed low inhibitory activity (millimolar IC50s). Conversely, the monomeric galactotriazole analogues were strong inhibitors of cholera toxin (IC50 = 71–75 μM).

  我们报道了一系列以1,2,3-三氮唑连接的二价半乳糖吡喃糖苷的合成，这些化合物可能作为霍乱毒素（CT）的抑制剂。对二价系列的抑制活性进行了检测（ELISA），结果显示其抑制活性较低（毫摩尔级别的IC50值）。相反，单体的半乳糖三氮唑类似物对霍乱毒素具有较强的抑制作用（IC50值为71-75微摩尔）。
• 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。
• Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues
  作者：Toshio Nishikawa、Yuya Koide、Shigeo Kajii、Kyoko Wada、Miyuki Ishikawa、Minoru Isobe

  DOI：10.1039/b414905j

  日期：——

  The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.

  通过 10 个步骤（包括以下关键步骤：甘露糖衍生物与链烷乙炔的 C-糖苷化反应、卡斯特罗吲哚合成、Sc(ClO4)3 促进与 L-丝氨酸衍生的氮丙啶羧酸酯偶联）从市售的δ-甲基-D-甘露糖苷中完全合成了δ-C-甘露糖基色氨酸（C-Man-Trp），这是一种天然的 C-糖基氨基酸。C-Man-Trp 的葡萄糖和半乳糖类似物也是用类似方法合成的。本文简要讨论了合成的 C-糖基色氨酸及其合成中间体的构象分析。
• Synthesis of 1,3- and 2,3-Diglycosylated Indoles as Potential Trisaccharide Mimetics
  作者：Till Opatz、Christine Wiebe、Silvia Fusté de la Sotilla

  DOI：10.1055/s-0031-1290761

  日期：2012.5

  Diglycosylated heteroaromatics may serve as metabolically stable mimetics of trisaccharides. Herein, the preparation of several 1,3- and 2,3-diglycosylindoles by direct C-glycosylation of monoglycosylated precursors is described.
• Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (<i>C</i>-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling
  作者：Alessandro Dondoni、Giandomenico Mariotti、Alberto Marra

  DOI：10.1021/jo020054m

  日期：2002.6.1

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.