3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol | 219864-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
• 英文别名: (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethyne；(2S,3S,4R,5S,6R)-2-ethynyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 219864-00-3
• 化学式: C₃₆H₃₆O₅
• 分子量: 548.679
• InChiKey: ODYZSGODFGXEDP-WGZBAJHCSA-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：

  3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol 在 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以81%的产率得到(2,3,4,6-tetra-O-benzyl-β-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：

  3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
  参考文献：
  名称：

  X-Ray Crystal Structure Determinations of Galactosylacetylene Building Blocks

  摘要：

  We report the crystal structures of two galactosylacetylenes: 3,7-anhydro-4,5,6,8-tetra- O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mann ooctitol (7) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol (8). A short overview of the synthetic chemistry used to obtain these targets is mentioned.

  DOI：

  10.1080/07328303.2011.554935

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）。
• Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins
  作者：Toshio Nishikawa、Yuya Koide、Akira Kanakubo、Hiroshi Yoshimura、Minoru Isobe

  DOI：10.1039/b516282c

  日期：——

  α-C-Mannosyltryptophan (α-C-Man-Trp) has been found to be a novel post-translational modification of tryptophan found from some biologically important glycoproteins. In order to analyze the biological functions of α-C-Man-Trp, we have developed an efficient synthetic strategy for α-C-Man-Trp and its glucose and galactose analogues, starting from α-C-glycosidation of the corresponding hexapyranoside derivatives with tinacetylene. According to the synthetic routes, we describe here syntheses of β-anomers of C-Man-Trp, and its glucose and galactose analogues from the corresponding β-C-glycosylacetylenes. During this study, we have developed a highly stereocontrolled synthesis of β-C-mannosylacetylene that is required for the synthesis of β-C-Man-Trp, while the precedented method gave an anomeric mixture of the C-mannosylacetylene. The synthetic C-Man-Trp and its analogues were analyzed by HPLC.

  α-C-甘露糖基色氨酸（α-C-Man-Trp）被发现是一种新的色氨酸翻译后修饰，存在于一些生物重要的糖蛋白中。为了分析α-C-Man-Trp的生物功能，我们开发了一种高效的合成策略，用于α-C-Man-Trp及其葡萄糖和半乳糖类似物，从对应的六糖派拉诺糖衍生物与乙炔锡的α-C-糖苷化反应开始。根据合成路线，我们在此描述了从相应的β-C-糖苷乙炔衍生物合成β-异构体的C-Man-Trp及其葡萄糖和半乳糖类似物。在这项研究中，我们开发了一种高度立体选择性合成β-C-甘露糖基乙炔的方法，这是合成β-C-Man-Trp所必需的，而先前的方法则给出了C-甘露糖基乙炔的异构体混合物。合成的C-Man-Trp及其类似物通过高效液相色谱（HPLC）进行了分析。
• Copper(I)-Catalyzed Azide-Alkyne Cycloadditions in Ionic Liquids under Amine-Free Conditions
  作者：Alberto Marra、Alessandro Dondoni、Alessandra Vecchi、Angela Chambery、Cinzia Chiappe

  DOI：10.1055/s-0029-1218760

  日期：2010.6

  Copper(I) iodide catalyzed cycloadditions of various combinations of structurally diverse organic azides and terminal alkynes were carried out in a commercially available, polyoxygenated ionic liquid (AMMOENG 100™) without addition of free amine. Unlike the previously tested ionic liquids, this solvent led exclusively to the 1,4-disubstituted triazole regioisomer. alkynes - azides - carbohydrates -

  在不添加游离胺的情况下，在市售的多氧化离子液体（AMMOENG 100™）中进行结构多样的有机叠氮化物和末端炔烃的各种组合的碘化亚铜（I）催化的环加成反应。与先前测试过的离子液体不同，该溶剂仅产生1,4-二取代的三唑区域异构体。 炔烃-叠氮化物-碳水化合物-铜-环加成
• Assembling Heterocycle-Tethered <i>C</i>-Glycosyl and α-Amino Acid Residues via 1,3-Dipolar Cycloaddition Reactions
  作者：Alessandro Dondoni、Pier Paolo Giovannini、Alessandro Massi

  DOI：10.1021/ol048963g

  日期：2004.8.1

  The 1,3-dipolar cycloadditions of C-glycosyl nitrile oxides and acetylenes to an alkyne and an azide, respectively, bearing a masked glycinyl moiety furnished disubstituted isoxazoles and triazoles. Unveiling the glycinyl group in these cycloadducts afforded C-glycosyl alpha-amino acids in which the two bioactive entities were tethered through rigid five-membered heterocycles. Optimized entries to

  C-糖基腈氧化物和乙炔的1，3-偶极环加成分别成炔基和叠氮化物，它们带有掩蔽的缩水甘油基部分，提供了二取代的异恶唑和三唑。在这些环加合物中揭示甘氨酸基团得到C-糖基α-氨基酸，其中两个生物活性实体通过刚性五元杂环束缚。相同化合物的最佳化合物包括使用未掩盖但受保护的含炔烃和叠氮化物的氨基酸作为1,3-偶极环加成反应的伙伴。
• Microwave-Enhanced Ionothermal CuAAC for the Synthesis of Glycoclusters on a Calix[4]arene Platform
  作者：Alessandra Vecchi、Bernardo Melai、Alberto Marra、Cinzia Chiappe、Alessandro Dondoni

  DOI：10.1021/jo800954z

  日期：2008.8.1

  i-Pr2EtN in three different ionic liquids, that is, [C8dabco][N(CN)2], [C8dabco][Br], and Ammoeng 110. Reactions were performed at 80 °C by thermal and MW dielectric heating. In all cases, multiple cycloadditions took place to give a triazole-linked tetra-C-galactosyl-calix[4]arene in up to 90% yield. The [C8dabco][N(CN)2] ionic liquid was also used to perform the multiclick reactions with propargyl

  四-叠氮基杯[4]芳烃衍生物被允许与乙炔基四反应ö苄基Ç中的CuI的存在和半乳糖苷我-Pr 2将EtN [C在三个不同的离子液体，即，8 DABCO] [N（CN）2 ]，[C 8 DABCO] [Br]和Ammoeng110。反应是通过热和MW介电加热在80°C进行的。在所有的情况下，多个环加成发生，得到三唑连接的四Ç半乳糖杯[4]中高达90％的产率芳烃。[C 8 DABCO] [N（CN）2 ]离子液体也用于与炔丙基O-乳糖苷和S-唾液甙。