1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucofuranose

• 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: 1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucofuranose
• 英文别名: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→3)-1:2,5:6-di-O-isopropylidene-α-D-glucofuranose；(2’,3’,4’,6’-tetra-O-benzoyl-β-D-galactopyranosyl)-(1’→3)-1,2,5,6-di-O-isopropylidene-α-D-glucofuranoside；2,3,4,6-tetra-O-benzoyl-β-D-galactopyranose-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；[(2R,3S,4S,5R,6S)-6-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₄₆H₄₆O₁₅
• 分子量: 838.862
• InChiKey: LQFYHQFHYMJIGQ-SEVJVZFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucofuranose 在 溶剂黄146 作用下， 反应 6.0h， 以83%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides

  摘要：

  为了开发潜在的抗真菌药剂，七种糖苷结合物由 a-L 鼠李糖、6-脱氧-a-L-塔尔糖、b-D-半乳糖、a-D-甘露糖、b-D-木糖-(1®4)-6-脱氧-a-L-塔尔糖、b-D-半乳糖-(1®4)-a-L-鼠李糖组成、以三氯乙酰亚氨酸糖基化合物为供体，高效、实用地合成了以 b-D-半乳糖-(1®3)-b-D-木糖-(1®4)-6-脱氧-a-L-塔罗糖为糖酮、齐墩果酸为苷元的新化合物。新化合物的结构已通过 MS、1H-NMR 和 13C NMR 得到证实。基于菌丝生长速率的初步研究表明，所有化合物都对 Sclerotinia sclerotiorum (Lib.) de Bary、Rhizoctonia solani Kuhn、Botrytis cinerea Pers 和 Phytophthora parasitica Dast 具有一定的杀菌活性。

  DOI：

  10.3390/molecules16021113
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate 、 双丙酮葡萄糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides

  摘要：

  为了开发潜在的抗真菌药剂，七种糖苷结合物由 a-L 鼠李糖、6-脱氧-a-L-塔尔糖、b-D-半乳糖、a-D-甘露糖、b-D-木糖-(1®4)-6-脱氧-a-L-塔尔糖、b-D-半乳糖-(1®4)-a-L-鼠李糖组成、以三氯乙酰亚氨酸糖基化合物为供体，高效、实用地合成了以 b-D-半乳糖-(1®3)-b-D-木糖-(1®4)-6-脱氧-a-L-塔罗糖为糖酮、齐墩果酸为苷元的新化合物。新化合物的结构已通过 MS、1H-NMR 和 13C NMR 得到证实。基于菌丝生长速率的初步研究表明，所有化合物都对 Sclerotinia sclerotiorum (Lib.) de Bary、Rhizoctonia solani Kuhn、Botrytis cinerea Pers 和 Phytophthora parasitica Dast 具有一定的杀菌活性。

  DOI：

  10.3390/molecules16021113

文献信息

• Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*
  作者：David Crich、Abhisek Banerjee、Wenju Li、Qingjia Yao

  DOI：10.1081/car-200066978

  日期：2005.8.1

  piperidine in the trifluoromethanesulfonic anhydride‐mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at −78°C as opposed to the −60°C required to keep 1‐benzenesulfinyl piperidine in solution. N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric

  描述了一种大规模生产1-苯磺酰基哌啶和其他亚磺酰胺的改进方案。结果表明，在三氟甲磺酸酐介导的硫糖苷活化中，1-苯亚磺酰基吡咯烷和N，N-二乙基苯亚磺酰胺的作用类似于1-苯亚磺酰基哌啶，而且它们的结晶性较弱，因此它们可在-78°C下使用到将1-苯亚磺酰基哌啶保持在溶液中所需的-60°C。N，N-二环己基苯磺酰胺不会与三氟甲磺酸酐结合活化硫糖苷，这归因于其较大的空间体积。*致谢Jacques H. Van Boom教授。
• Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives
  作者：Ben W. Greatrex、Alison M. Daines、Sarah Hook、Dirk H. Lenz、Warren McBurney、Thomas Rades、Phillip M. Rendle

  DOI：10.1002/open.201500149

  日期：2015.12

  formulated, while C‐28 choline ester derivatives preferred self‐assembly and did not interact with the liposomes. When alone and in the presence of cholesterol and phospholipid, the choline ester derivatives produced nanocrystalline rods or helical micelles. The effects of modifying sugar stereochemistry and the aglycone on the immunostimulatory effects of the saponins was then evaluated using the activation

  为了发现一种新的合成疫苗佐剂，进行了二十三碳精，gypsogenin和齐墩果酸受体与二糖和三糖供体的糖基化反应，以生成一系列天然产物QS-21的模拟物。将皂苷与磷脂酰胆碱和胆固醇一起配制，并通过透射电子显微镜分析其结构。3‐ O‐（Man p（1 → 3）Glc p角姜黄素配制成时会产生大量环状胶束，而C-28胆碱酯衍生物更倾向于自组装且不与脂质体相互作用。当单独存在胆固醇和磷脂时，胆碱酯衍生物会产生纳米晶棒或螺旋胶束。然后使用激活标记MHC II类和CD86在小鼠骨髓树突状细胞中评估了修饰糖的立体化学和糖苷配基对皂苷的免疫刺激作用的作用。活性最高的皂苷3‐ O‐（Man p（1 → 3）Glc p）七面发生素在细胞培养物中高浓度时具有刺激性，但在体内并没有转化为强烈的反应。
• Facile synthesis of triterpenoid saponins bearing β-Glu/Gal-(1→3)-β-GluA methyl ester and their cytotoxic activities
  作者：Jian Gao、Xia Li、Guofeng Gu、Shanshan Liu、Min Cui、Hong-Xiang Lou

  DOI：10.1016/j.bmcl.2012.02.032

  日期：2012.4

  Convenient synthetic strategy toward spinasaponin A methyl ester 1 and calenduloside G methyl ester 2, two natural oleanane-type triterpenoid saponins bearing an unique beta-D-glucosyl/galactosyl-(1 -> 3)-beta-D-glucuronic acid methyl ester disaccharide moiety, was established. Based on this facile approach, four structurally modified congeners 3-6 with ursolic acid and glycyrrhetinic acid as aglycones were efficiently synthesized. MTT assay revealed the cytotoxicities against cancer cells of the synthesized saponins were varied with the change of aglycones and sugar units. Saponin 2 possessing the most potent cytotoxic effects could induce apoptosis of MCF-7 cells, which was detected by confocal micrographs using DAPI staining and flow cytometry using Annexin V and PI double staining. Furthermore, 2-induced apoptosis in MCF-7 cells was associated with ROS generation and loss of the mitochondria membrane potential (Delta psi(m)). (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Analogues of (1 → 6)‐Branched (1 → 3)‐Glucohexaose
  作者：Wei Zhao、Fanzuo Kong

  DOI：10.1081/car-200045260

  日期：2004.1

  beta-D-Galp-(1-->3)-[beta-D-Galp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 16 and beta-D-Galp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 18 were synthesized as the analogues of the immunomodulator beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)-]D-Glcp through coupling of trisaccharide donors 8 and 13 with trisaccharide acceptor 14 followed by deprotection, respectively.
• Thiourea-Cu(OTf)2/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors
  作者：Zuowa Li、Wenyan Shen、Changyu Cao、Zhaoyan Wang、Yaosheng Zhang、Weihua Xue

  DOI：10.1039/d4ob00064a

  日期：——

  NIS with a catalytic amount of thiourea and Cu(OTf) composes a powerful activator system for 2-azidoselenoglycoside and thioglycoside donors, allowing stereoselective glycosylation of alcoholic receptors to furnish the expected glycosides.