3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol | 219826-01-4

• 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: 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-triacetoxy-6-ethynyl-tetrahydropyran-2-yl]methyl acetate；3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,2-dideoxy-D-glycero-L-manno-oct-1-ynitol；[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-ethynyloxan-2-yl]methyl acetate
• CAS: 219826-01-4
• 化学式: C₁₆H₂₀O₉
• 分子量: 356.329
• InChiKey: HAVBGJDVNNVPRE-XFIYOXNOSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  403.363±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.273±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (2S,3S,4S,5S,6R)-6-((benzoyloxy)methyl)-2-ethynyl-5-hydroxytetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  带有刚性葡萄糖单击间隔子的强效二价抑制剂，用于铜绿假单胞菌凝集素LecA。

  摘要：

  描述了基于碳水化合物-三唑重复单元的新型刚性间隔基的合成及其掺入二价系统的过程。抑制研究表明，带有刚性末端和柔性末端的匹配系统可最有效地抑制铜绿假单胞菌凝集素LecA。

  DOI：

  10.1039/c2cc30234a
• 作为产物：
  描述：

  2,3,4,6-四-O-(苯基甲基)-D-半乳糖酸 D-内酯 在 三乙基硅烷 、 sodium hydroxide 、 正丁基锂 、 cerium(III) chloride 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 77.25h， 生成 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
  参考文献：
  名称：

  Novel Type of Rigid C-Linked Glycosylacetylene−Phenylalanine Building Blocks for Combinatorial Synthesis of C-linked Glycopeptides

  摘要：

  C-linked 3- and 4-(glycosylacetylene)-Fmoc-phenylalanines were synthesized as rigid building blocks for synthesis of libraries of neoglycopeptide templates. Perbenzylated 1,5-galactonolactone, 1,5-gluconolactone, and 1,5-mannonolactone were reacted with cerium TMS-acetylide and the products reduced to the C-glycosylacetylene-TMS derivatives. The gluco and galacto configurations yielded exclusively the beta-C-glycoside, whereas the mannonolactone gave a mixture of alpha-C- and beta-C-anomer. The products were subjected to acetolysis and TMS cleavage. The resulting peracetylated glycosylacetylenes were cross-coupled with the (R,S)-N-alpha-acetyl-3- and 4-iodophenylalanine O-methyl esters by Pd(0) catalysis in piperidine to give the eight possible C-linked glycosyl amino acid building blocks 33-40 as diastereomeric pairs. These were O-deacetylated. As an example of further conversion into neoglycopeptide templates the N-acetyl group of the 4-linked galacto-diastereomeric pair 43 was hydrolyzed selectively by acylase 1 and separated from the (R)stereoisomer. The product was converted to 4-(beta-C-galactosylacetylene)(N-alpha-Fmoc-)-L-phenylalanine (52) by reaction with Fmoc-OSu. Acid hydrolysis of galactosyl acetylene phenyl alanine 43 at elevated temperature afforded the conversion of the acetylene to the 1'-oxo derivative which was also N-alpha-Fmoc protected. The building blocks were used in the glycopeptide synthesis of three neoglycopeptide templates 54, 55, and 56 known to bind to murine MHC class II E-k and to present the glycan for interaction with the T-cell receptor. This template has previously been employed to elicit a carbohydrate specific T-cell response.

  DOI：

  10.1021/jo980517h

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 Sugar-Based Silica Gels by Copper-Catalysed Azide-Alkyne Cycloaddition via a Single-Step Azido-Activated Silica Intermediate and the Use of the Gels in Hydrophilic Interaction Chromatography
  作者：Lisa Moni、Alessia Ciogli、Ilaria D'Acquarica、Alessandro Dondoni、Francesco Gasparrini、Alberto Marra

  DOI：10.1002/chem.201000106

  日期：2010.5.17

  Novel sugar‐based silica gels were prepared by exploiting the copper‐catalysed azide–alkyne cycloaddition (CuAAC) of two different sugar alkynes, namely, ethynyl C‐galactoside 1 and propargyl O‐lactoside 2, with new single‐step azido‐activated silica gels. The fully characterised stationary phases were generally used for hydrophilic interaction chromatography (HILIC), with particular application in

  新颖的基于糖-二氧化硅凝胶通过利用两种不同的糖炔烃组成的铜催化的叠氮化物-炔烃环加成加成（CuAAC），即，乙炔基制备Ç半乳糖苷1和炔丙基Ò -β-乳糖苷2，以及新型的一步式叠氮活化硅胶。完全表征的固定相通常用于亲水相互作用色谱法（HILIC），特别用于单糖的立体选择性分离。进行了动态HILIC（DHILIC）实验，以评估诱变对两种相互转化的糖异构体的色谱峰形状的影响。分离其他高极性化合物（包括氨基酸和类黄酮）可显示出这种材料的潜力。
• 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。