2,3,4-Tri-O-benzoyl-6-desoxy-α-D-galactopyranose | 141115-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-Tri-O-benzoyl-6-desoxy-α-D-galactopyranose
• 英文别名: 2,3,4-Tri-O-benzoyl-α-D-fucopyranose；(3R,4S,5S,6R)-2-hydroxy-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate；2,3,4-tri-O-benzoyl-alpha-d-fucopyranose；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-hydroxy-2-methyloxan-3-yl] benzoate
• CAS: 141115-70-0
• 化学式: C₂₇H₂₄O₈
• 分子量: 476.483
• InChiKey: UTEZHORWKBBBND-LPVFLTEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-Tri-O-benzoyl-6-desoxy-α-D-galactopyranose 在 2,6-二叔丁基吡啶 、 silver trifluoromethanesulfonate 、 溴化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (2R,3R,4S,5S,6R)-2-(((4aR,6S,7R,8R,8aS)-7-(1,3-dioxoisoindolin-2-yl)-6-(ethylthio)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Spijker, Nynke M.; Boeckel, Constant A. A. van, Angewandte Chemie, 1991, vol. 103, # 2, p. 179 - 182

  摘要：

  DOI：
• 作为产物：
  描述：

  D-Fucose 在 吡啶 、 二甲胺 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 生成 2,3,4-Tri-O-benzoyl-6-desoxy-α-D-galactopyranose
  参考文献：
  名称：

  Parasite glycoconjugates. Part 11.1 Preparation of phosphodisaccharide synthetic probes, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania

  摘要：

  在糖基化反应中使用柯尼希斯康诺尔法和三氯乙酰亚氨酸法，在表聚反应中使用三氟丙烯酯的 SN2 亲核置换法，在磷酸化反应中使用糖基膦酸氢盐法，合成了一组磷酸二糖（底物类似物），用于研究利什曼原虫生物合成酶的受体底物特异性。

  DOI：

  10.1039/b004653l

文献信息

• Process for the production of peracylated 1-0-glycosides
  申请人：Schering AG

  公开号：US20030069402A1

  公开（公告）日：2003-04-10

  The invention relates to a process for the production of peracylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar is a monosaccharide that is functionalized in 1-OH-position, R represents methyl, ethyl, propyl, isopropyl, tbutyl, phenyl, n means 2, 3 or 4, X means —COO— or —NH—and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of peracylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  该发明涉及一种生产通式I的过酰化1-O-糖苷或其盐的工艺，其中糖是在1-OH位置上被官能化的单糖，R代表甲基、乙基、丙基、异丙基、叔丁基、苯基，n取2、3或4，X代表—COO—或—NH—，L代表一条直链、分支、饱和或不饱和的C1-C30碳链，该碳链可以被基团中断或取代。根据该发明的工艺从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产具有1-O官能化侧链的过酰化糖苷。
• α-bisabolol β-D-fucopyranoside as a potential modulator of β-amyloid peptide induced neurotoxicity: An in vitro & in silico study
  作者：Mahalingam Jeyakumar、Sethuraman Sathya、Soniya Gandhi、Prabhakarrao Tharra、Venkatesan Suryanarayanan、Sanjeev Kumar Singh、Beeraiah Baire、Kasi Pandima Devi

  DOI：10.1016/j.bioorg.2019.102935

  日期：2019.7

  strategy for the management of AD. In view of this, the present study was designed to synthesize and evaluate the multifunctional neuroprotective ability of the sesquiterpene glycoside α-bisabolol β-D-fucopyranoside (ABFP) against multiple targets like acetylcholinesterase, oxidative stress and β-amyloid peptide aggregation induced cytotoxicity. In silico computational docking and simulation studies

  阿尔茨海默氏病（AD）是影响老年人的多方面神经退行性疾病。对于AD治疗，现有药物无效，因为这些药物仅减轻疾病症状。由于AD的发展涉及多种病理蛋白，寻找针对多种AD蛋白的单个分子将是AD管理的新策略。有鉴于此，本研究旨在合成和评估倍半萜烯糖苷α-bisabololβ-D-岩藻糖苷（ABFP）对多个靶标如乙酰胆碱酯酶，氧化应激和β-淀粉样肽聚集诱导的细胞毒性的多功能神经保护能力。在计算机上用乙酰胆碱酯酶（AChE）对ABFP进行计算机对接和模拟研究表明，它可以与该酶的Asp74和Thr75残基相互作用。体外研究表明，该化合物除具有抗氧化，抗聚集和解聚特性外，还具有抑制AChE酶的显着能力。另外，分子动力学模拟研究证明Aβ肽和ABFP之间的相互作用残基被发现与Leu34和Ile31有关。此外，该化合物能够保护Neuro2 a细胞免受Aβ25-35肽诱导的毒性。总的来说，本研究显然证明了ABFP是
• Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues
  作者：Marianne Piochon、Jean Legault、Charles Gauthier、André Pichette

  DOI：10.1016/j.phytochem.2008.11.013

  日期：2009.1

  alpha-Bisabolol beta-D-fucopyranoside, a cytotoxic naturally occurring compound, was efficiently synthesized along with five other alpha-bisabolol glycosides (beta-D-glucoside, beta-D-galactoside, alpha-D-mannoside, beta-D-Xyloside and alpha-L-rhamnoside). Glycosidation of ot-bisabolol was performed using Schmidt's inverse procedure and provided excellent yields (83-95%). Cytotoxicity was evaluated against a broad panel of cancerous cell lines including human and rat glioma (U-87, U-251 and GL-261) since the anticancer activity of alpha-bisabolol was previously demonstrated against brain tumor cell lines. The addition of a sugar moiety markedly increased alpha-bisabolol cytotoxicity in most cases. Among the synthesized glycosides, alpha-bisabolol alpha-L-rhamnopyranoside exhibited the strongest cytotoxic activity with IC50 ranging from 40 to 64 mu M. According to ADME in silico predictions, this glycoside closely respects physicochemical parameters necessary to cross the blood-brain barrier passively. (C) 2008 Elsevier Ltd. All rights reserved.
• US6831164B2
  申请人：——

  公开号：US6831164B2

  公开（公告）日：2004-12-14
• Parasite glycoconjugates. Part 11.1 Preparation of phosphodisaccharide synthetic probes, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
  作者：Andrew J. Ross、Irina A. Ivanova、Michael A. J. Ferguson、Andrei V. Nikolaev

  DOI：10.1039/b004653l

  日期：——

  A set of phosphodisaccharides, substrate analogues, which will be used to study acceptor–substrate specificity of the Leishmania biosynthetic enzymes, are synthesized using the Koenigs–Knorr and trichloroacetimidate methods for the glycosylation reactions, SN2 nucleophilic displacement of a triflic ester for epimerization, and the glycosyl hydrogenphosphonate method for phosphorylation.

  在糖基化反应中使用柯尼希斯康诺尔法和三氯乙酰亚氨酸法，在表聚反应中使用三氟丙烯酯的 SN2 亲核置换法，在磷酸化反应中使用糖基膦酸氢盐法，合成了一组磷酸二糖（底物类似物），用于研究利什曼原虫生物合成酶的受体底物特异性。