苯基 alpha-D-吡喃甘露糖苷 | 21797-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯基 alpha-D-吡喃甘露糖苷
• 中文别名: 苯基alpha-D-吡喃甘露糖苷
• 英文名称: phenyl α-D-mannoopyranoside
• 英文别名: phenyl α-D-mannopyranoside；phenyl α-D-mannoside；phenyl-α-D-mannopyranoside；Phenyl-α-D-mannopyranosid；phenyl-α-D-mannoside；Phenyl α-D-mannopyranose；Phenyl alpha-D-mannopyranoside；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
• CAS: 21797-50-2
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: NEZJDVYDSZTRFS-GCHJQGSQSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  482.1±45.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯基 alpha-D-吡喃甘露糖苷 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 110.25h， 生成 phenyl-α-D-mannopyranosyl-(1->6)-α-D-mannopyranoside
  参考文献：
  名称：

  Building Up Key Segments of N-Glycans in the Gas Phase:  Intrinsic Structural Preferences of the α(1,3) and α(1,6) Dimannosides

  摘要：

  The intrinsic conformer specific vibrational spectra of two important subunits of the core pentasaccharide of Winked glycans, the alpha(1,3) and alpha(1,6) dimannosides, have been recorded in the gas phase. Coupling these measurements with a computational exploration of their conformational landscapes has enabled their conformational assignment and has identified characteristic vibrational signatures associated with particular conformational families-including those that do or do not display inter-ring hydrogen bonding across the glycosidic linkage. In addition, the IR spectra of the monosaccharide moieties provide benchmarks, through which the conformational assignments can be refined. This introduces a general concept of modularity and secondary structure in oligosaccharides-essential for the success of similar studies on larger oligosaccharides in the future.

  DOI：

  10.1021/ja055891v
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 以65%的产率得到苯基 alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  FimH Antagonists for the Oral Treatment of Urinary Tract Infections: From Design and Synthesis to in Vitro and in Vivo Evaluation

  摘要：

  Urinary tract infection (UTI) by uropathogenic Escherichia coli (UPEC) is one of the most common infections, particularly affecting women. The interaction of FimH, a lectin located at the tip of bacterial pill, with high mannose structures is critical for the ability of UPEC to colonize and invade the bladder epithelium. We describe the synthesis and the in vitro/in vivo evaluation of alpha-D-mannosides with the ability to block the bacteria/host cell interaction. According to the pharmacokinetic properties, a prodrug approach for their evaluation in the UTI mouse model was explored. As a result, an orally available, low molecular weight FimH antagonist was identified with the potential to reduce the colony forming units (CFU) in the urine by 2 orders of magnitude and in the bladder by 4 orders of magnitude. With FimH antagonist 16b, the great potential for the effective treatment of urinary tract infections with a new class of orally available antiinfectives could be demonstrated.

  DOI：

  10.1021/jm101011y

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES
  申请人：UNIV WASHINGTON

  公开号：WO2011050323A1

  公开（公告）日：2011-04-28

  The present invention encompasses compounds and methods for treating urinary tract infections.

  本发明包括用于治疗尿路感染的化合物和方法。
• A Simple Synthesis of Methyl 2,3,6- and 2,4,6-Tri-<i>O</i>-benzyl-α-D-mannosides
  作者：Shinkiti Koto、Kazuhiro Takenaka、Naohiko Morishima、Akiko Sugimoto、Shonosuke Zen

  DOI：10.1246/bcsj.57.3603

  日期：1984.12

  Cotrolled benzylation of methyl α-D-mannopyranoside with benzyl chloride and LiOH selectively gave the 2,3,6-tribenzyl ether in a 53% yield. Such a reaction using benzyl chloride and KOH afforded mainly the 2,4,6-tribenzyl ether in a 41% yield. The products were allylated and then hydrolyzed to give the corresponding 1-OH derivatives.

  用苄基氯和 LiOH 控制甲基 α-D-吡喃甘露糖苷的苄基化反应，选择性地得到 2,3,6-三苄基醚，产率为 53%。使用苄基氯和KOH的这种反应主要以41%的产率提供2,4,6-三苄基醚。产物被烯丙基化，然后水解得到相应的1-OH衍生物。
• Methods And Systems For Growing Plants Using Silicate-Based Substrates, Cultivation Of Enhanced Photosynthetic Productivity And Photosafening By Utilization Of Exogenous Glycopyranosides For Endogenous Glycopyranosyl-Protein Derivatives, And Formulations, Processes And Systems For The Same
  申请人：Innovation Hammer, LLC

  公开号：US20140331555A1

  公开（公告）日：2014-11-13

  Methods for promoting plant growth based on novel photosafening treatment regimes with glycopyranosides including glycopyranosylglycopyranosides, and aryl-a-D-glycopyranosides, and more specifically, with one or more compounds comprising terminal mannosyl-triose, optionally in the presence of light enhanced by one or more light reflecting and/or refracting members such as silicon-based substrates. Furthermore, chemical synthesis processes for the above compounds are disclosed for general application to plants. Silicate microbeads of the like are distributed over the ground or substrate in which roots of a plant are supported and planted, beneath and around a plant in a manner that light is refracted or reflected toward the phylloplane.

  基于新型光保护处理方案促进植物生长的方法，包括甘露聚糖苷类化合物，如甘露聚糖苷和芳基-a-D-甘露聚糖苷，更具体地，使用含有端基甘露三糖的一个或多个化合物，可选地在存在硅基基底等一个或多个反射和/或折射光的成员的情况下增强光线。此外，还公开了上述化合物的化学合成过程，以供普遍应用于植物。类似的硅酸盐微珠分布在植物的根部支撑和种植的地面或基质上，在植物的下方和周围，使光线以折射或反射的方式朝向叶面。
• Phenyl glycosides – Solid-state NMR, X-ray diffraction and conformational analysis using genetic algorithm
  作者：Piotr Wałejko、Jarosław Bukowicki、Łukasz Dobrzycki、Paweł Socha、Katarzyna Paradowska

  DOI：10.1016/j.chemphys.2018.12.001

  日期：2019.3

  The X-ray structures of 2,6-dimethylphenyl and phenyl 2,3,4,6-tetra-O-acetyl β-glucosides (1 and 3) and phenyl α-mannoside (6) were obtained. The independent part of the unit cell of the glycosides 1 and 6 was formed by one molecule, and for the glucoside 3, two molecules in the crystal cell were observed. In deacetylated glycosides 4 and 6 the crystal structure was established by a hydrogen bond network

  获得了2,6-二甲基苯基和苯基2,3,4,6-四-O-乙酰基β-葡萄糖苷（1和3）和苯基α-甘露糖苷（6）的X射线结构。糖苷1和6的晶胞的独立部分由一个分子形成，对于糖苷3，在晶胞中观察到两个分子。在去乙酰化的糖苷4和6中，晶体结构是由糖羟基和溶剂分子之间形成的氢键网络建立的。在13芳基糖苷的ÇCPMAS NMR谱1 - 6被分析。在3的光谱中，观察到C4芳基信号加倍，这证实了固体样品中存在两个独立的分子。GAAGS（遗传算法辅助网格搜索）方法用于确定α-甘露糖苷和β-葡萄糖苷的低能构象体。使用分子力学（MMFF94）和量子力学理论（DFT，B3LYP / 6-31 + G（d，p））计算芳基侧基的取向。
• Reactions of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-α-d-erythro-hex-2-enopyranoside and its phenyl analogue with sodium methoxide
  作者：Tohru Sakakibara、Azuma Yamamoto、Yoshiharu Ishido

  DOI：10.1016/0008-6215(88)84111-9

  日期：1988.8

  Abstract Reaction of the title methyl glycoside 5 with methanolic sodium methoxide afforded mainly the isomeric α- d - erythro -hex-3-enopyranoside derivative 13 , formed by migration of the double bond from C-2 to C-3, together with 1,5-anhydro-4,6- O -benzylidene-2-deoxy-3- O -methyl-2- C - p -tolylsulfonyl- d - ribo -hex-1-enitol ( 7 ) and the methyl 4,6- O -benzylidene-3- O -methyl-2- C - p -tolylsulfonyl-α-

  摘要标题甲基糖苷5与甲醇钠甲醇溶液反应，主要得到由C-2到C-3的双键迁移形成的异构体α-d-赤型-hex-3-enopyranoside衍生物13，以及1， 5-脱水-4,6-O-亚苄基-2-脱氧-3-O-甲基-2-C-对甲苯磺酰基-d-核糖-己-1-烯醇（7）和甲基4,6-O -亚苄基-3-O-甲基-2-C-对甲苯基磺酰基-α-d-己吡喃糖苷，其具有葡萄糖（15），同素（14）和altro（12）构型。苯基糖苷类似物（6）为5的类似反应导致苯基损失，得到7和12-14以及苯基4,6-O-亚苄基-2-脱氧-3-O-甲基-2-C -对-甲苯磺酰基-α-d-葡吡喃糖苷（18）。